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Merck
CN

690600

Sigma-Aldrich

N-[3,5-双(三氟甲基)苯基]-N′-[(9R)-6′-甲氧基-9-金鸡宁]硫脲

≥90.0%

别名:

1-[3,5-双(三氟甲基)苯基)-3-{(R)(6-甲氧基-4-喹啉基)-[(2R,4S,5R)-5-乙烯基-1-氮杂-二环[2.2.2]辛-2-基]甲基}硫脲, epi-N-奎宁基-N′-双(3,5-三氟甲基)苯硫脲

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关于此项目

经验公式（希尔记法）:
C29H28F6N4OS
化学文摘社编号:
852913-25-8
分子量:
594.61
MDL编号:
MFCD16621389
UNSPSC代码:
12352005
PubChem化学物质编号:
329761352

主要文件

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方案

≥90.0% (HPLC)
≥90.0%

表单

lumps

官能团

amine
fluoro
thiourea

SMILES字符串

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

一般描述

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

应用

采用双官能金鸡纳有机催化剂，进行硝基甲烷的高度对映选择性共轭加成反应，生成查耳酮
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.

特点和优势

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

包装

Bottomless glass bottle. Contents are inside inserted fused cone.

象形图

Skull and crossbones
GHS06

警示用语：

Danger

危险声明

H301

预防措施声明

P301 + P310

危险分类

Acute Tox. 3 Oral

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCCB2863
BCBV0736
BCBT0407
BCBP6007V
BCBJ9001V

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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)
The growing role of organocatalysis in asymmetric synthesis.
Aldrichimica Acta, 44(1), 16-16 (2011)
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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