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Merck
CN
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文件

安全信息

392723

Sigma-Aldrich

(DHQ)2PHAL

≥95%

别名:

氢化奎宁 1,4-(2,3-二氮杂萘)二醚

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About This Item

经验公式（希尔记法）:
C48H54N6O4
CAS号:
140924-50-1
分子量:
778.98
Beilstein:
5475677
MDL编号:
MFCD00191975
UNSPSC代码:
12352005
PubChem化学物质编号:
24864480
NACRES:
NA.22

质量水平

200

检测方案

≥95%

旋光性

[α]22/D +336°, c = 1.2 in methanol

mp

178 °C (dec.) (lit.)

SMILES字符串

CC[C@@H]1CN2CCC1CC2[C@H](Oc3nnc(O[C@@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10

InChI

1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30+,31-,32+,43-,44-,45-,46-/m1/s1

InChI key

YUCBLVFHJWOYDN-PPIALRKJSA-N

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相关类别

一般描述

DHQ)2PHAL is a modified cinchona alkaloid.

应用

Sharpless 不对称双羟基化的配体，用于由 (E,E)- 或 (E,Z)-1,3-二烯酸甲酯不对称制备 syn-3,5-羟基羧酸酯。
(DHQ)2PHAL may be used in the following processes:
  • As a catalyst Asymmetric and chemoselective N-allylic alkylation of indoles with Morita-Baylis-Hillman carbonates to form pyrrolo[1,2-a]indole and pyrrolo[3,2,1-ij]quinoline derivatives.
  • As a ligand for the osmium catalyzed-Sharpless asymmetric dihydroxylation step of (S)-a-benzoyloxy carboxylic acids multistep synthesis.
  • As a ligand for the carbamate based asymmetric aminohydroxylation of styrene derivatives to form N-carbamate protected R-arylglycinols.

外形

具有三取代 C=C 键的不饱和酯的不对称双羟基化。

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H317

预防措施声明

P280 - P302 + P352

危险分类

Skin Sens. 1

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type N95 (US)

法规信息

监管及禁止进口产品

分析证书(COA)

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From styrenes to enantiopure a-arylglycines in two steps.
Reddy KL and Sharpless KB.
Journal of the American Chemical Society, 120(6), 1207-1217 (1990)
Regioselective Oxidative Cleavage of Benzylidene Acetals: Synthesis of a-and ?-Benzoyloxy Carboxylic Acids.
Kumar PS, et al.
Angewandte Chemie (International Edition in English), 49(4), 804-807 (2010)
Chemoselective Asymmetric N-Allylic Alkylation of Indoles with Morita-Baylis-Hillman Carbonates.
Cui H-L, et al.
Angewandte Chemie (International Edition in English), 48(31), 5737-5740 (2009)
Kapferer, Tobias; Brueckner, Reinhard
European Journal of Organic Chemistry, 9, 2119-2133 (2006)
Md Moinuddin Ahmed et al.
The Journal of organic chemistry, 71(20), 7741-7746 (2006-09-26)
The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting

商品

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。

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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