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Merck
CN

456713

(DHQD)2AQN

95%

别名:

氢化奎尼丁(蒽醌-1,4-二基)二醚

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关于此项目

经验公式(希尔记法):
C54H56N4O6
化学文摘社编号:
分子量:
857.05
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
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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

SMILES string

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 key

ARCFYUDCVYJQRN-ZPCQJLRDSA-N

assay

95%

form

solid

optical activity

[α]/D -498°

mp

165 °C (lit.)

General description

(DHQD)2AQN is a biscinchona alkaloid.

Application

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.

Legal Information

经 Rhodia Pharma Solutions 授权销售。

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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分析证书(COA)

Lot/Batch Number

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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)
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
Eecker, H. Sharpless, K.B.
Angewandte Chemie (International Edition in English), 35, 448-448 (1996)

商品

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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