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文件

374482

N-苄基奎宁氯

Name: <I>N</I>-苄基奎宁氯
Brand: ALDRICH

95%

别名:

QUIBEC

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About This Item

经验公式（希尔记法）:

C₂₇H₃₁ClN₂O₂

CAS号:

67174-25-8

分子量:

451.00

Beilstein:

5702637

MDL编号:

MFCD00198105

UNSPSC代码:

12352005

PubChem化学物质编号:

24863311

NACRES:

NA.22

质量水平

100

检测方案

95%

旋光性

[α]20/D −235°, c = 1.5 in H₂O

mp

200-205 °C (dec.) (lit.)

SMILES字符串

[Cl-].COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@+]3(C[C@@H]4C=C)Cc5ccccc5)c2c1

InChI

1S/C27H31N2O2.ClH/c1-3-20-18-29(17-19-7-5-4-6-8-19)14-12-21(20)15-26(29)27(30)23-11-13-28-25-10-9-22(31-2)16-24(23)25;/h3-11,13,16,20-21,26-27,30H,1,12,14-15,17-18H2,2H3;1H/q+1;/p-1/t20-,21-,26-,27+,29+;/m0./s1

InChI key

JYDIJFKNXHPWBJ-GOGFHWEMSA-M

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一般描述

N-Benzylquininium chloride (or Quibec) belongs to the class of cinchona family of alkaloids. It is used as a catalyst in the presence of hydroxide bases in various phase transfer reactions, epoxidations, alkylations, and Michael reactions.

应用

N-Benzylquininium chloride can be used as a phase transfer catalyst:

In the sulfenylation of various β-keto sulfoxides.
To synthesize N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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Phase-Transfer-Catalyzed Asymmetric Aza-Henry Reaction Using N-Carbamoyl Imines Generated In Situ from ?-Amido Sulfones

Fini F, et al.

Angewandte Chemie (International ed. in English), 44(48), 7975-7978 (2005)

N-Benzylquininium Chloride

Bos Mary E, et al.

Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-7 (2001)

Sulfenylation of β-keto sulfoxides. III. Diastereoselectivity induced by a chiral phase transfer catalyst

Wladislaw B, et al.

Tetrahedron, 55(41), 12023-12030 (1999)

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