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Merck
CN

456713

(DHQD)2AQN

95%

Synonym(s):

Hydroquinidine (anthraquinone-1,4-diyl) diether

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About This Item

Empirical Formula (Hill Notation):
C54H56N4O6
CAS Number:
176298-44-5
Molecular Weight:
857.05
NACRES:
NA.22
PubChem Substance ID:
329756886
UNSPSC Code:
12352005
MDL number:
MFCD00467216

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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

(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.
Superior ligand for asymmetric dihydroxylation reactions of most olefins bearing aliphatic substituents or olefins having heteroatoms in the allylic position.

Legal Information

Sold under license from Rhodia Pharma Solutions.

Storage Class

11 - 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV1031V
MKBP4480V
MKBG0430
MKBD4504
MKBB3123

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

Articles

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.

金鸡纳生物碱

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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