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Merck
CN

857270

Sigma-Aldrich

(+)-辛可宁

85%

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别名:
辛可宁 单盐酸盐 二水合物
经验公式(希尔记法):
C19H22N2O
CAS号:
分子量:
294.39
Beilstein:
89689
EC 号:
MDL编号:
UNSPSC代码:
12352104
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

85%

形式

solid

旋光性

[α]23/D +228°, c = 0.5 in ethanol

mp

258-260 °C (lit.)

SMILES字符串

[H][C@@]12CCN(C[C@H]1C=C)[C@]([H])(C2)[C@@H](O)c3ccnc4ccccc34

InChI

1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1

InChI key

KMPWYEUPVWOPIM-QAMTZSDWSA-N

一般描述

(+)-Cinchonine, one of the alkaloids found in the barks of cinchona tree, is mainly used in the treatment of malaria. It belongs to the monoclinic crystal system and P21 space group. The solubility of cinchonine can be improved by the formation of inclusion complexes with cyclodextrins.

应用

(+)-Cinchonine, in the presence of lithium diisopropylamide (LDA) forms a complex, which can catalyze the asymmetric conjugate addition of benzyl- and alkylphosphonates to aromatic and heteroaromatic nitroalkenes to form the corresponding adducts.

其他说明

残留二氢金鸡宁

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Acute Tox. 4 Oral - Skin Sens. 1A

WGK

WGK 1

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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The molecular and crystal structure of the alkaloid cinchonine.
Oleksyn B, et al.
Acta Crystallographica Section B, Structural Science, 35(2), 440-444 (1979)
Cinchonine catalyzed diastereo-and enantioselective Michael addition of a-lithiated phosphonates to nitroalkenes.
Rai V, et al.
Tetrahedron Asymmetry, 18(22), 2719-2726 (2007)
Song CE.
Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis, 2-3 (2009)
Jiabing Jiang et al.
Journal of chromatography. A, 1218(24), 3763-3770 (2011-05-11)
We designed and synthesized a cinchonine derivative to be used as a novel chiral monomer. It was employed in a dual role of functional monomer and cross-linking monomer, displaying multi-binding sites for the template (S)-ketoprofen. Monodisperse molecularly imprinted core-shell microspheres
Wei Chen et al.
Organic & biomolecular chemistry, 5(5), 816-821 (2007-02-23)
The C3-selective enantioselective Michael-type Friedel-Crafts alkylations of indoles with nonchelating alpha,beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to

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