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Merck
CN
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文件

安全信息

456713

Sigma-Aldrich

(DHQD)2AQN

95%

别名:

氢化奎尼丁(蒽醌-1,4-二基)二醚

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About This Item

经验公式（希尔记法）:
C54H56N4O6
CAS号:
176298-44-5
分子量:
857.05
MDL编号:
MFCD00467216
UNSPSC代码:
12352005
PubChem化学物质编号:
329756886
NACRES:
NA.22

检测方案

95%

形式

solid

旋光性

[α]/D -498°

mp

165 °C (lit.)

SMILES字符串

CC[C@@H]1CN2CCC1CC2[C@@H](Oc3ccc(O[C@H](C4CC5CCN4C[C@H]5CC)c6ccnc7ccc(OC)cc67)c8C(=O)c9ccccc9C(=O)c38)c%10ccnc%11ccc(OC)cc%10%11

InChI

1S/C54H56N4O6/c1-5-31-29-57-23-19-33(31)25-45(57)53(39-17-21-55-43-13-11-35(61-3)27-41(39)43)63-47-15-16-48(50-49(47)51(59)37-9-7-8-10-38(37)52(50)60)64-54(46-26-34-20-24-58(46)30-32(34)6-2)40-18-22-56-44-14-12-36(62-4)28-42(40)44/h7-18,21-22,27-28,31-34,45-46,53-54H,5-6,19-20,23-26,29-30H2,1-4H3/t31-,32-,33+,34+,45-,46-,53+,54+/m1/s1

InChI key

ARCFYUDCVYJQRN-ZPCQJLRDSA-N

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一般描述

(DHQD)2AQN is a biscinchona alkaloid.

应用

用于大多数含脂肪族取代基的烯烃或者烯丙基位置具有杂原子的烯烃的不对称双羟基化反应的优良配体。
(DHQD)2AQN may be used to:
  • Catalyze the asymmetric cyanation of ketones to form tertiary cyanohydrin carbonates.
  • Facilitate the asymmetric ring opening of terminal N-nosylaziridines with trimethylsilyl cyanide.

法律信息

经 Rhodia Pharma Solutions 授权销售。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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A highly enantioselective chiral Lewis base-catalyzed asymmetric cyanation of ketones.
Tian SK and Deng L.
Journal of the American Chemical Society, 123(25), 6195-6196 (2001)
Michael Wilking et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(51), 18601-18607 (2016-10-12)
The cinchona alkaloid dimer (DHQD)2 PHAL has been shown to be a broadly applicable catalyst for asymmetric halogenations. However, this catalyst does not have to be dimeric and a class of monomeric quinidine and quinine-derived catalysts was prepared, often showing
Asymmetric recognition and sequential ring opening of 2-substituted-N-nosylaziridines with (DHQD) 2AQN and TMSNu.
Minakata S, et al.
Organic & Biomolecular Chemistry, 7(4), 641-643 (2009)
Eecker, H. Sharpless, K.B.
Angewandte Chemie (International Edition in English), 35, 448-448 (1996)

商品

金鸡纳生物碱

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Cinchona Alkaloids

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.

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