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Merck
CN

359580

(8S,9R)-(−)-N-Benzylcinchonidinium chloride

98%

Synonym(s):

N-Benzylcinchonidinium chloride, BCDC

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About This Item

Empirical Formula (Hill Notation):
C26H29ClN2O
CAS Number:
Molecular Weight:
420.97
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
273-938-3
Beilstein/REAXYS Number:
5421832
MDL number:
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InChI key

FCHYSBWCOKEPNQ-IOPLZPHGSA-M

InChI

1S/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20-,21-,25-,26+,28?;/m0./s1

SMILES string

[Cl-].O[C@@H]([C@@H]1C[C@@H]2CC[N+]1(C[C@@H]2C=C)Cc3ccccc3)c4ccnc5ccccc45

assay

98%

form

powder

optical activity

[α]20/D −180°, c = 1.3 in H2O

mp

210 °C (dec.) (lit.)

functional group

hydroxyl, phenyl

Other Notes

Chiral phase transfer catalyst;resolutions by crystallization of the inclusion complex

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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F Toda et al.
The Journal of Organic Chemistry, 59, 5748-5748 (1994)
C.M. Gasparski, M.J. Miller
Tetrahedron, 47, 5367-5367 (1991)
J.H. Zhang et al.
Tetrahedron Asymmetry, 13, 1363-1363 (2002)
S. Julia et al.
Journal of the Chemical Society. Perkin Transactions 1, 574-574 (1981)

Articles

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

不对称相转移催化(PTC)已被公认为是许多均相合成有机转化的“绿色”替代方法,并且已被广泛应用。合成修饰的金鸡纳生物碱是用于不对称PTC的典型手性有机催化剂。

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