Standard Article

Electrophilic Selenium/Tellurium Reagents: Reactivity and their Contribution to Green Chemistry

Organic Selenium and Tellurium (2013)

  1. Claudio Santi,
  2. Caterina Tidei

Published Online: 17 JUN 2013

DOI: 10.1002/9780470682531.pat0720

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Santi, C. and Tidei, C. 2013. Electrophilic Selenium/Tellurium Reagents: Reactivity and their Contribution to Green Chemistry. Patai's Chemistry of Functional Groups. .

Author Information

  1. Group of Catalysis and Green Chemistry, Department of Chemistry and Technology of Drugs, University of Perugia, Perugia, Italy

Publication History

  1. Published Online: 17 JUN 2013

Chemistry Terms

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Abstract

Selenium moieties are conveniently introduced into an organic molecule using electrophilic selenenylating reagents and the process is generally highly chemo-, regio and stereoselective requiring mild experimental conditions. In addition, organoselenium derivatives can be directly converted into a number of different functional groups and the organoselenium moiety can be employed for further stereoselective manipulation of the molecule. Several applications are described for the inter- and intramolecular carbon–oxygen, carbon–nitrogen and carbon–carbon bond formation as well as for the α-functionalization of carbonyl derivatives and the nucleophilic aromatic substitution reactions. More recently, the development of simple and efficient procedures for the preparation of chiral selenium reagents allowed their successful application in electrophilic asymmetric synthesis. Nowadays, probably the most recent aspect of this kind of chemistry is correlated with some new reactions that can be effected using organoselenium compounds as catalysts in renewable or alternative non-toxic media (water, glycerol, ionic liquids) bringing this kind of research in line with the concept of ‘Green and Sustainable Chemistry’. During the last half century, the application of tellurium reagents has undergone a notable improvement, overcoming the reluctance of several researchers mainly due to the characteristic persistent smell of many tellurium derivatives. In this chapter some general aspects of the chemistry promoted by electrophilic selenium and tellurium compounds are described exploiting also the differences between these two reagents.

Keywords:

  • selenium;
  • tellurium;
  • electrophile;
  • addition;
  • cyclization;
  • green chemistry;
  • catalysis;
  • heterocycles;
  • asymmetric synthesis;
  • stereoselective

Featured Compounds

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  1. 1 - 250
Compound 2
Molecular Weight:235.97
Molecular Formula:C6H5BrSe
InChIKey:LCEFEIBEOBPPSJ-UHFFFAOYSA-N
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Compound 3
Molecular Weight:191.52
Molecular Formula:C6H5ClSe
InChIKey:WJCXADMLESSGRI-UHFFFAOYSA-N
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Compound 1
Molecular Weight:312.13
Molecular Formula:C12H10Se2
InChIKey:Not Available
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Compound 4
Molecular Weight:301.03
Molecular Formula:C6H5F6PSe
InChIKey:JOFIFJDDRYDTTG-UHFFFAOYSA-O
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Compound 5
Molecular Weight:391.81
Molecular Formula:C6H5F6SbSe
InChIKey:AMMCIQSPPVUBDX-UHFFFAOYSA-I
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Compound 6
Molecular Weight:327.26
Molecular Formula:C13H12O3SSe
InChIKey:HMCZJQJCBZYWBA-UHFFFAOYSA-N
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Compound 7
Molecular Weight:305.13
Molecular Formula:C7H5F3O3SSe
InChIKey:WSBBSYJIJBSMBB-UHFFFAOYSA-N
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Compound 8
Molecular Weight:385.14
Molecular Formula:C13H9NO3Se2
InChIKey:VQPBCLVQTACBQG-UHFFFAOYSA-N
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9a
Molecular Weight:270.16
Molecular Formula:C6H9NO4SSe
InChIKey:LFFZIFDYLKGCCF-UHFFFAOYSA-N
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Compound 9b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:93.99
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:158.86
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:308.03
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:114.41
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:VGVHNLRUAMRIEW-UHFFFAOYSA-N
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Compound 25
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:VGVHNLRUAMRIEW-UHFFFAOYSA-N
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Compound 19
Molecular Weight:190.12
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 20
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:RKSNPTXBQXBXDJ-UHFFFAOYSA-N
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:326.29
Molecular Formula:C18H17NSe
InChIKey:RUELCGHUJHDNMR-AWEZNQCLSA-N
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Compound 26
Molecular Weight:267.23
Molecular Formula:C13H16OSe
InChIKey:VPSSGIRDGZROEH-NKUHCKNESA-N
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Compound 27
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:RKSNPTXBQXBXDJ-UHFFFAOYSA-N
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Compound 30
Molecular Weight:254.349
Molecular Formula:C12H18N2O2S
InChIKey:FVQOPNPBJBMFPC-NSHDSACASA-N
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Compound 31
Molecular Weight:246.348
Molecular Formula:C15H22N2O
InChIKey:SKHPYKHVYFTIOI-PUODRLBUSA-N
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Compound 28
Molecular Weight:86.1356
Molecular Formula:C4H10N2
InChIKey:IZBNHIWUATWXHK-BYPYZUCNSA-N
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Compound 29
Molecular Weight:232.224
Molecular Formula:C6H11F3N2O2S
InChIKey:RIWFUAUXWIEOTK-YFKPBYRVSA-N
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Compound 32
Molecular Weight:597.5119
Molecular Formula:C24H23F12NOSi
InChIKey:MOHRGTBNEJKFMB-IBGZPJMESA-N
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Compound 33
Molecular Weight:325.52
Molecular Formula:C20H27NOSi
InChIKey:Not Available
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Compound 34
Molecular Weight:397.554
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35
Molecular Weight:338.397
Molecular Formula:C21H22O4
InChIKey:AFCFIEIENKVPNB-BUHFOSPRSA-N
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Compound 36
Molecular Weight:493.45
Molecular Formula:C27H26O4Se
InChIKey:TVINTSVOTJDGPZ-VHEBQXMUSA-N
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Compound 37
Molecular Weight:336.3811
Molecular Formula:C21H20O4
InChIKey:AMAVXXZCOGAHTO-UHFFFAOYSA-N
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Compound 38
Molecular Weight:322.3976
Molecular Formula:C21H22O3
InChIKey:AYLUSPNSCWEODJ-BUHFOSPRSA-N
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Compound 39
Molecular Weight:302.3664
Molecular Formula:C21H18O2
InChIKey:HTKUMJHHQCCWAR-UHFFFAOYSA-N
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Compound 40
Molecular Weight:84.14
Molecular Formula:C4H4S
InChIKey:YTPLMLYBLZKORZ-UHFFFAOYSA-N
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:324.18
Molecular Formula:C8H6S2Se2
InChIKey:NLKLUGVCAPFMIE-UHFFFAOYSA-N
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Compound 46
Molecular Weight:567.39
Molecular Formula:C16H10S4Se3
InChIKey:HNWGNZLENKTIPN-UHFFFAOYSA-N
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Compound 47
Molecular Weight:68.074
Molecular Formula:C4H4O
InChIKey:YLQBMQCUIZJEEH-UHFFFAOYSA-N
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Compound 48
Molecular Weight:390.24
Molecular Formula:C12H8OS2Se2
InChIKey:JQAPSCLPGNMGFO-UHFFFAOYSA-N
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Compound 50
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 55
Molecular Weight:263.19
Molecular Formula:C13H12OSe
InChIKey:NNXSGISAOBFVLS-UHFFFAOYSA-N
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Compound 56
Molecular Weight:275.25
Molecular Formula:C15H16Se
InChIKey:FCIBJNLIOPZWGO-UHFFFAOYSA-N
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Compound 57
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:RDOXTESZEPMUJZ-UHFFFAOYSA-N
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Compound 58
Molecular Weight:293.22
Molecular Formula:C14H14O2Se
InChIKey:LURBCACEKXUJEG-UHFFFAOYSA-N
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Compound 408
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:295.67
Molecular Formula:C14H13ClSe
InChIKey:GFUKYWRENTUMJF-AWEZNQCLSA-N
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Compound 61
Molecular Weight:295.67
Molecular Formula:C14H13ClSe
InChIKey:BYGJRAMOADSZGI-AWEZNQCLSA-N
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Compound 64
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound 132
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound 408a
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound 67
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72
Molecular Weight:460.37
Molecular Formula:C20H30O2Se2
InChIKey:KTWZAHIINCJAIR-GOYBPXGQSA-N
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Compound 73
Molecular Weight:464.4
Molecular Formula:C20H34O2Se2
InChIKey:IORAJZGAXXQVAF-LGLNWZQNSA-N
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Compound 74
Molecular Weight:796.5
Molecular Formula:C32H32F10O2Se2
InChIKey:HUSZNONSFZUOEH-ARPMDMGNSA-N
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Compound 75
Molecular Weight:436.44
Molecular Formula:C20H38Se2
InChIKey:VZCUXRISYZDEIR-XETNVZRVSA-N
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 76a
Molecular Weight:400.23
Molecular Formula:C16H18O2Se2
InChIKey:UXRATEPHZGNOGD-RYUDHWBXSA-N
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Compound 76b
Molecular Weight:460.28
Molecular Formula:C18H22O4Se2
InChIKey:XQCKNSJYDLHJTO-RYUDHWBXSA-N
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Compound 76c
Molecular Weight:460.42
Molecular Formula:C18H22S2Se2
InChIKey:IZOGLAMCPKVHIF-KBPBESRZSA-N
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Compound 76d
Molecular Weight:520.47
Molecular Formula:C20H26O2S2Se2
InChIKey:YALLNNCSXLVHIT-KBPBESRZSA-N
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Compound 76e
Molecular Weight:454.37
Molecular Formula:C20H28N2Se2
InChIKey:YVRKOVPFNYBODE-HOTGVXAUSA-N
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Compound 76f
Molecular Weight:514.42
Molecular Formula:C22H32N2O2Se2
InChIKey:ROPJXRKSWCNOQV-HOTGVXAUSA-N
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Compound 77
Molecular Weight:634.61
Molecular Formula:C34H40N2Se2
InChIKey:HCXWMWWHHFJTHV-KMKVIZFGSA-N
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Compound 78
Molecular Weight:660.61
Molecular Formula:C34H38N4Se2
InChIKey:LXAILLULADGJKN-CUPIEXAXSA-N
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Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:291.25
Molecular Formula:C15H16OSe
InChIKey:UKALKFJPGZKHBR-UHFFFAOYSA-N
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Compound 83
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 84
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 85
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 87
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 88
Molecular Weight:327.26
Molecular Formula:C10H16O5SSe
InChIKey:WJHNNVQCPRLXHJ-MXMVMAASSA-N
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Compound 89
Molecular Weight:547.32
Molecular Formula:C17H16F8O4SSe
InChIKey:FJBYUMOPAGSBTM-XGEHTFHBSA-N
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Compound 90
Molecular Weight:349.19
Molecular Formula:C9H9F3O4SSe
InChIKey:ZJSUNYWJLWDNDS-LURJTMIESA-N
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Compound 91
Molecular Weight:379.21
Molecular Formula:C10H11F3O5SSe
InChIKey:LLNXHITUHZYHLM-LURJTMIESA-N
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Compound 92
Molecular Weight:379.28
Molecular Formula:C10H11F3O3S2Se
InChIKey:LKRPBXKFHZEZGJ-ZETCQYMHSA-N
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Compound 93
Molecular Weight:409.3
Molecular Formula:C11H13F3O4S2Se
InChIKey:IFQOAVLKVXBSRQ-ZETCQYMHSA-N
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Compound 94
Molecular Weight:376.25
Molecular Formula:C11H14F3NO3SSe
InChIKey:AXTHZDANBBTQKE-MRVPVSSYSA-N
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Compound 95
Molecular Weight:324.26
Molecular Formula:C10H15NO4SSe
InChIKey:NBDBBTRBIBBEIN-MRVPVSSYSA-N
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Compound 96
Molecular Weight:466.38
Molecular Formula:C18H20F3NO3SSe
InChIKey:GZEPPHWTRGOPLU-ZIAGYGMSSA-N
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Compound 97
Molecular Weight:414.38
Molecular Formula:C17H21NO4SSe
InChIKey:SKXPSUCNJFZFOI-ZIAGYGMSSA-N
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Compound 98
Molecular Weight:427.38
Molecular Formula:C17H20N2O4SSe
InChIKey:WWRFAPIVFWRPEA-IRXDYDNUSA-N
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Compound 99
Molecular Weight:409.3
Molecular Formula:C11H13F3O4S2Se
InChIKey:QUQDIDWHPYCZDL-UHFFFAOYSA-N
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Compound 100
Molecular Weight:421.25
Molecular Formula:C12H13F3O6SSe
InChIKey:JENQBTAAFKYIIU-QMMMGPOBSA-N
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Compound 101
Molecular Weight:481.34
Molecular Formula:C15H21F3O7SSe
InChIKey:SQSIZKHCIAPVMB-GHMZBOCLSA-N
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Compound 102
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:VOEDRUGFNJEWGQ-VMPITWQZSA-N
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Compound 103
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:WIZDDEMKPVYLOF-CMDGGOBGSA-N
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Compound 104
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:ZIJWGEHOVHJHKB-BQYQJAHWSA-N
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Compound 105
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (S)-106
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:ZIJWGEHOVHJHKB-FLOXNTQESA-N
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Compound (R)-106
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:Not Available
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Compound 107
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:IRMJSPUTNYPVMB-KOLCDFICSA-N
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Compound 108
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:PZKFYTOLVRCMOA-UHFFFAOYSA-N
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Compound 110
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 111
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:BWHOZHOGCMHOBV-BQYQJAHWSA-N
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Compound 115
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:MBAOABFNWSOOLU-CMDGGOBGSA-N
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Compound 113
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 114
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 117
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 118
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 119
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 120
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 121
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:BUDQDWGNQVEFAC-UHFFFAOYSA-N
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Compound 122
Molecular Weight:214.2598
Molecular Formula:C14H14O2
InChIKey:IHPDTPWNFBQHEB-KBPBESRZSA-N
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Compound 123
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 124
Molecular Weight:134.1305
Molecular Formula:C5H10O4
InChIKey:ZTOHRSGVYZXRGQ-WDCZJNDASA-N
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Compound 125
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound 126
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 127
Molecular Weight:164.1565
Molecular Formula:C6H12O5
InChIKey:IMPKVMRTXBRHRB-DPJOLKNXSA-N
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Compound 128
Molecular Weight:180.1559
Molecular Formula:C6H12O6
InChIKey:CDAISMWEOUEBRE-NIPYSYMMSA-N
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Compound 129
Molecular Weight:285.4238
Molecular Formula:C19H27NO
InChIKey:LVXNOENXICRUOP-LAVNZNGBSA-N
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Compound 131
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 133
Molecular Weight:277.22
Molecular Formula:C14H14OSe
InChIKey:RKLQIYWNDDRJHD-UHFFFAOYSA-N
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Compound 134
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:CTMHWPIWNRWQEG-UHFFFAOYSA-N
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Compound 135
Molecular Weight:269.24
Molecular Formula:C13H18OSe
InChIKey:AOPJSXWUWRLBMZ-CHWSQXEVSA-N
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Compound 136
Molecular Weight:154.2924
Molecular Formula:C11H22
InChIKey:JOHIXGUTSXXADV-HWKANZROSA-N
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Compound 137
Molecular Weight:327.36
Molecular Formula:C17H28OSe
InChIKey:OJOJJLFTVOZEEY-DOTOQJQBSA-N
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Compound 138
Molecular Weight:390.32
Molecular Formula:C17H28Se2
InChIKey:Not Available
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Compound 139
Molecular Weight:168.319
Molecular Formula:C12H24
InChIKey:SMDXUIYTBVHJNX-UHFFFAOYSA-N
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Compound 140
Molecular Weight:323.37
Molecular Formula:C18H28Se
InChIKey:XNRJQBYTWRLASZ-LGMDPLHJSA-N
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Compound 142
Molecular Weight:323.37
Molecular Formula:C18H28Se
InChIKey:AQCNODLCSJTUGI-UHFFFAOYSA-N
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Compound 144
Molecular Weight:184.3184
Molecular Formula:C12H24O
InChIKey:AEGYYOYVMBSGLF-UHFFFAOYSA-N
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Compound 145
Molecular Weight:324.455
Molecular Formula:C19H32O4
InChIKey:IOACXHQAHJPHGO-VDNIMJPMSA-N
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Compound 146
Molecular Weight:340.4544
Molecular Formula:C19H32O5
InChIKey:WKJOUJVEOVLBHV-XUNAUSDWSA-N
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Compound 147
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 148
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 149
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:BQOFWKZOCNGFEC-BDAKNGLRSA-N
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Compound 151
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:FAMJUFMHYAFYNU-JTQLQIEISA-N
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Compound 153
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:ITYNGVSTWVVPIC-XVIXHAIJSA-N
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Compound 150
Molecular Weight:309.31
Molecular Formula:C16H22OSe
InChIKey:TYCGXPMVKJZBTQ-HLPPOEQASA-N
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Compound 152
Molecular Weight:311.32
Molecular Formula:C16H24OSe
InChIKey:CBDBKVCXIINDGL-FVQBIDKESA-N
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Compound 154
Molecular Weight:377.42
Molecular Formula:C21H30OSe
InChIKey:ZZJGGEWCAQLJMJ-BATASMPNSA-N
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Compound 155
Molecular Weight:357.31
Molecular Formula:C10H14O5S2Se
InChIKey:WIGQQHQETBQCEA-ZETCQYMHSA-N
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Compound 156
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-QHHAFSJGSA-N
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Compound 158
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 157
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 159
Molecular Weight:140.2658
Molecular Formula:C10H20
InChIKey:UURSXESKOOOTOV-MDZDMXLPSA-N
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Compound 160
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 161
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 162a
Molecular Weight:166.24
Molecular Formula:C9H10OS
InChIKey:RLLJHMBTZSGFAS-UHFFFAOYSA-N
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Compound 163
Molecular Weight:351.32
Molecular Formula:C16H16O2SSe
InChIKey:RONAPVVHIAMDBQ-FOWTUZBSSA-N
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Compound 162b
Molecular Weight:242.2528
Molecular Formula:C15H15OP
InChIKey:PGPAPANRSWMTQO-UHFFFAOYSA-N
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Compound 164
Molecular Weight:429.33
Molecular Formula:C22H21O2PSe
InChIKey:QGOHOUCZBWLEPQ-OQKWZONESA-N
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Compound 165
Molecular Weight:356.6276
Molecular Formula:C26H44
InChIKey:FBFVQHLOYZMQCS-JLHYTZGSSA-N
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Compound 166
Molecular Weight:600.78
Molecular Formula:C35H55NO2Se
InChIKey:JDSXFCPCOQBHEQ-WYHWUVBZSA-N
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Compound 167
Molecular Weight:445.7207
Molecular Formula:C29H51NO2
InChIKey:JEVRBFTZMGLYRX-PLHIVNTJSA-N
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Compound 168
Molecular Weight:443.7049
Molecular Formula:C29H49NO2
InChIKey:WOJLVXDSFZWSKC-PLHIVNTJSA-N
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Compound 169
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:Not Available
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Compound 314
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:Not Available
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Compound 170
Molecular Weight:460.33
Molecular Formula:C21H22N2Se2
InChIKey:FUFQQHXXDMVJBV-FXELSEDVSA-N
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Compound 171
Molecular Weight:460.33
Molecular Formula:C21H22N2Se2
InChIKey:NJDBYCUYSJEIKZ-XRXFAXGQSA-N
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Compound 172
Molecular Weight:140.2658
Molecular Formula:C10H20
InChIKey:UURSXESKOOOTOV-MDZDMXLPSA-N
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Compound 173
Molecular Weight:428.51
Molecular Formula:C22H39NO2Se
InChIKey:ZXVHJCUOEYMIMY-UEJCCDMKSA-N
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Compound 174
Molecular Weight:428.51
Molecular Formula:C22H39NO2Se
InChIKey:ZXVHJCUOEYMIMY-WPJAAHMASA-N
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Compound (4R,5R)-177
Molecular Weight:197.3171
Molecular Formula:C12H23NO
InChIKey:YCNZRFCPZDEIHL-VXGBXAGGSA-N
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Compound (4R,5R)-178
Molecular Weight:213.383
Molecular Formula:C12H23NS
InChIKey:KRLMZGUMMJKOEA-VXGBXAGGSA-N
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Compound (4S,5S)-177
Molecular Weight:197.3171
Molecular Formula:C12H23NO
InChIKey:YCNZRFCPZDEIHL-RYUDHWBXSA-N
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Compound (4S,5S)-178
Molecular Weight:213.383
Molecular Formula:C12H23NS
InChIKey:KRLMZGUMMJKOEA-RYUDHWBXSA-N
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Compound 179
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:JHRXFDOUKQYGPW-JXMROGBWSA-N
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Compound 180
Molecular Weight:388.37
Molecular Formula:C19H23N3OSe
InChIKey:OXFZBEDLNFMZLC-MSOLQXFVSA-N
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Compound 181
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 182
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 183
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:OADZSDHBFLIAPX-JTQLQIEISA-N
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Compound 184
Molecular Weight:223.2698
Molecular Formula:C15H13NO
InChIKey:TZBCQZDVMUNWPG-LBAUFKAWSA-N
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Compound 185
Molecular Weight:289.2866
Molecular Formula:C14H15N3O4
InChIKey:PPBTVNLZWBZWDH-VIFPVBQESA-N
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Compound 186
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound 187
Molecular Weight:532.4
Molecular Formula:C22H26N6Se2
InChIKey:LPKFCADUJGPDIC-MNAPGUCWSA-N
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Compound 188
Molecular Weight:532.4
Molecular Formula:C22H26N6Se2
InChIKey:LPKFCADUJGPDIC-KDXIVRHGSA-N
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Compound 189
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 190
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 413
Molecular Weight:114.2609
Molecular Formula:C6H14Si
InChIKey:HYWCXWRMUZYRPH-UHFFFAOYSA-N
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Compound 192
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 193
Molecular Weight:421.29
Molecular Formula:C13H18F3O5SSe
InChIKey:FCSDEPBDGPHFJG-VTLYIQCISA-N
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Compound 194
Molecular Weight:543.55
Molecular Formula:C29H36O5Se
InChIKey:URSRZUFAWLBMRR-PRIXLJELSA-N
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Compound 195
Molecular Weight:496.54
Molecular Formula:C28H35NO2Se
InChIKey:UBMLUVLXXYSEGX-NLDIKOHWSA-N
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Compound 198
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 199
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 200
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 201
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 202
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 203
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 204
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 205
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 196
Molecular Weight:362.21
Molecular Formula:C15H23BrSe
InChIKey:MVIBVXIRTTVWLV-UHFFFAOYSA-N
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Compound (anti E) (197)
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (anti Z) (197)
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (syn E) (197)
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (syn Z) (197)
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 207
Molecular Weight:375.32
Molecular Formula:C19H20O3Se
InChIKey:UANHOEBGYYPXPC-NKGKWGDASA-N
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Compound 210
Molecular Weight:375.32
Molecular Formula:C19H20O3Se
InChIKey:UANHOEBGYYPXPC-MGHWNKPDSA-N
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Compound 211
Molecular Weight:218.2485
Molecular Formula:C13H14O3
InChIKey:VANSFNWOVSTMGA-SKDRFNHKSA-N
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Compound 212
Molecular Weight:218.2485
Molecular Formula:C13H14O3
InChIKey:VANSFNWOVSTMGA-CABZTGNLSA-N
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Compound 208
Molecular Weight:375.32
Molecular Formula:C19H20O3Se
InChIKey:UANHOEBGYYPXPC-NBMRYCAZSA-N
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Compound 209
Molecular Weight:375.32
Molecular Formula:C19H20O3Se
InChIKey:UANHOEBGYYPXPC-XFKAJCMBSA-N
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Compound (erythro) (206)
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:MXAHTGJUQPFFAG-UEUCCFLYSA-N
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Compound (threo) (206)
Molecular Weight:220.2643
Molecular Formula:C13H16O3
InChIKey:MXAHTGJUQPFFAG-HNFQPOCMSA-N
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Compound 213
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:VTIODUHBZHNXFP-NSCUHMNNSA-N
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Compound 216
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:VTIODUHBZHNXFP-IHWYPQMZSA-N
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Compound 214
Molecular Weight:255.21
Molecular Formula:C12H16OSe
InChIKey:GWBRJAIQTFLNQZ-PWSUYJOCSA-N
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Compound 215
Molecular Weight:255.21
Molecular Formula:C12H16OSe
InChIKey:GWBRJAIQTFLNQZ-JQWIXIFHSA-N
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Compound 217
Molecular Weight:255.21
Molecular Formula:C12H16OSe
InChIKey:PEYIPXRLUVDUIX-JQWIXIFHSA-N
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Compound 218
Molecular Weight:255.21
Molecular Formula:C12H16OSe
InChIKey:PEYIPXRLUVDUIX-PWSUYJOCSA-N
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Compound 220
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound 219
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:AWMVMTVKBNGEAK-QMMMGPOBSA-N
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Compound 221
Molecular Weight:317.28
Molecular Formula:C17H18OSe
InChIKey:OKDYXYLLTYDYPI-RDJZCZTQSA-N
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Compound 222
Molecular Weight:317.28
Molecular Formula:C17H18OSe
InChIKey:OKDYXYLLTYDYPI-WBVHZDCISA-N
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Compound 223
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MAPLHIRYLFONGA-KOLCDFICSA-N
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Compound 224
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MAPLHIRYLFONGA-ONGXEEELSA-N
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Compound 225
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:NIKBSMYNKTUHIF-GFVADAIESA-N
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Compound 226
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:NIKBSMYNKTUHIF-FGEFZZPRSA-N
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Compound 227
Molecular Weight:319.26
Molecular Formula:C16H16O2Se
InChIKey:GJMCQSDBRQIFKN-PMPSAXMXSA-N
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Compound 228
Molecular Weight:319.26
Molecular Formula:C16H16O2Se
InChIKey:GJMCQSDBRQIFKN-BZUAXINKSA-N
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Compound 229
Molecular Weight:319.26
Molecular Formula:C16H16O2Se
InChIKey:GJMCQSDBRQIFKN-OAGGEKHMSA-N
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Compound 230
Molecular Weight:319.26
Molecular Formula:C16H16O2Se
InChIKey:GJMCQSDBRQIFKN-OWCLPIDISA-N
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Compound 231
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:RGUGOJLATFSMSG-XQQFMLRXSA-N
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Compound 232
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:RGUGOJLATFSMSG-UPJWGTAASA-N
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Compound 233
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:RGUGOJLATFSMSG-YNEHKIRRSA-N
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Compound 234
Molecular Weight:359.32
Molecular Formula:C19H20O2Se
InChIKey:KALHNQNJJNEXRY-HCXYKTFWSA-N
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Compound 235
Molecular Weight:312.426
Molecular Formula:C19H20O2S
InChIKey:YGLLSCGWOCJZFJ-OFJUMYTHSA-N
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Compound 236
Molecular Weight:359.32
Molecular Formula:C19H20O2Se
InChIKey:KALHNQNJJNEXRY-FCGDIQPGSA-N
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Compound 237
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:DPCMFIRORYQTCL-NSCUHMNNSA-N
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Compound 238
Molecular Weight:361.34
Molecular Formula:C19H22O2Se
InChIKey:VNQLUIJRDPIPLD-UHFFFAOYSA-N
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Compound 239
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:WZZCBQYAYBNPNO-UHFFFAOYSA-N
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Compound 240
Molecular Weight:528.4
Molecular Formula:C26H26O2Se2
InChIKey:CHCQUFDOLFDJGR-UHFFFAOYSA-N
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Compound 241
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:VTUMZIFGQBQRIX-UHFFFAOYSA-N
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Compound 242
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 243
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:HTMSBPUVAYCQMP-UHFFFAOYSA-N
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Compound 244
Molecular Weight:351.3
Molecular Formula:C17H20O3Se
InChIKey:SMYCTLNUPOAHJJ-UHFFFAOYSA-N
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Compound 245
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 248
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 247a
Molecular Weight:331.27
Molecular Formula:C17H16O2Se
InChIKey:ICLCNGUKDOAKQV-NCOADZHNSA-N
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Compound 247b
Molecular Weight:410.16
Molecular Formula:C17H15BrO2Se
InChIKey:RGKCWAYIOZXXMM-NCOADZHNSA-N
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