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690600

Sigma-Aldrich

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea

≥90.0%

Synonym(s):

1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(R)(6-methoxy-4-quinolinyl)-[(2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl]methyl}thiourea, epi-N-Quinidyl-N′-bis(3,5-trifluoromethyl)phenylthiourea

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About This Item

Empirical Formula (Hill Notation):
C29H28F6N4OS
CAS Number:
852913-25-8
Molecular Weight:
594.61
MDL number:
MFCD16621389
UNSPSC Code:
12352005
PubChem Substance ID:
329761352

assay

≥90.0% (HPLC)
≥90.0%

form

lumps

functional group

amine
fluoro
thiourea

SMILES string

COc1ccc2nccc([C@@H](NC(=S)Nc3cc(cc(c3)C(F)(F)F)C(F)(F)F)C4CC5CCN4C[C@@H]5C=C)c2c1

InChI

1S/C29H28F6N4OS/c1-3-16-15-39-9-7-17(16)10-25(39)26(22-6-8-36-24-5-4-21(40-2)14-23(22)24)38-27(41)37-20-12-18(28(30,31)32)11-19(13-20)29(33,34)35/h3-6,8,11-14,16-17,25-26H,1,7,9-10,15H2,2H3,(H2,37,38,41)/t16-,17-,25+,26+/m0/s1

InChI key

IQMKPBFOEWWDIQ-ZRJNXXGPSA-N

General description

The product is a cinchona-alkaloid-derived, bifunctional catalyst containing a thiourea group at position 9.

Application

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea may be used to catalyze the formation of optically active Mannich adducts from stable N-carbamate amido sulfones via enantioselective Mannich reaction.[1]
Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts[2][3]

Features and Benefits

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea as an organocatalyst has the following advantages over transition-metal catalysis:[4]
  • Lower toxicity
  • Lower costs
  • Air and moisture stability for simple reaction setup

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB2863
BCBV0736
BCBT0407
BCBP6007V
BCBJ9001V

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The growing role of organocatalysis in asymmetric synthesis.
Aldrichimica Acta, 44(1), 16-16 (2011)
Asymmetric Mannich reactions with in situ generation of carbamate-protected imines by an organic catalyst.
Song J, et al.
Organic Letters, 9(4), 603-606 (2007)
Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance.
Séamus H McCooey et al.
Angewandte Chemie (International ed. in English), 44(39), 6367-6370 (2005-09-02)
Benedek Vakulya et al.
Organic letters, 7(10), 1967-1969 (2005-05-07)
Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields.

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