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685879

Sigma-Aldrich

(1S,2S)-1,2-双(2-羟苯基)乙二胺

95%

别名:

(1S,2S)-1,2-双(2-羟苯基)-1,2-乙二胺

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About This Item

经验公式（希尔记法）:
C14H16N2O2
分子量:
244.29
MDL编号:
MFCD09751761
UNSPSC代码:
12352116
PubChem化学物质编号:
24885691
NACRES:
NA.22

质量水平

100

方案

95%

表单

solid

旋光性

[α]22/D -65°, c = 0.2 in chloroform

mp

157-162 °C

官能团

amine

SMILES字符串

N[C@H]([C@@H](N)c1ccccc1O)c2ccccc2O

InChI

1S/C14H16N2O2/c15-13(9-5-1-3-7-11(9)17)14(16)10-6-2-4-8-12(10)18/h1-8,13-14,17-18H,15-16H2/t13-,14-/m0/s1

InChI key

MRNPLGLZBUDMRE-KBPBESRZSA-N

相关类别

一般描述

1,2-Bis(2-hydroxyphenyl)ethylenediamine is a chiral diamine, which acts as a key precursor (mother diamine) in the synthesis of alkyl, aryl, and heterocyclic diamines (daughter diamines), used for various synthetic applications.

应用

(1S,2S)-1,2-Bis(2-hydroxyphenyl)ethylenediamine can be used:
  • As a starting material for the synthesis of Schiff base complexes of gold(III), bearing potent anticancer activity.
  • As a stereoinductor in the synthesis of quinoline and isoquinoline based 1,2-diamines; that are employed as catalysts in the preparation of warfarin and coumachlor in water.

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H302

危险分类

Acute Tox. 4 Oral

储存分类代码

11 - Combustible Solids

WGK

WGK 3

个人防护装备

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCT9810
MKCS9009
MKCS9039
MKCV2696
MKCS2454

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Mimicking nature to make unnatural amino acids and chiral diamines
So SM, et al.
European Journal of Organic Chemistry, 2012(2), 229-241 (2012)
Synthesis and biological evaluation of gold (III) Schiff base complexes for the treatment of hepatocellular carcinoma through attenuating TrxR activity
Bian M, et al.
European Journal of Medicinal Chemistry, 193(36), 112234-112234 (2020)
Green asymmetric synthesis of Warfarin and Coumachlor in pure water catalyzed by quinoline-derived 1, 2-diamines
Kucherenko AS, et al.
Green Chemistry, 20(3), 754-759 (2018)
Stereospecific synthesis of C 2 symmetric diamines from the mother diamine by resonance-assisted hydrogen-bond directed diaza-Cope rearrangement.
Kim H, et al.
Journal of the American Chemical Society, 130(36), 12184-12191 (2008)

商品

Chiral Vicinal Diamines for Asymmetric Synthesis

Chiral vicinal diamines are of tremendous interest to the synthetic chemist as they are found in many chiral catalysts and pharmaceuticals.

相关内容

Chin Group – Professor Product Portal

The Chin group is interested in computational and experimental approaches to understanding stereoselective recognition and catalysis. Their studies in weak forces (H-bonding, electronic and steric effects) has led to a highly efficient method for making limitless varieties of chiral vicinal diamines from the 'mother diamine' that are useful for developing stereoselective organocatalysts or transition metal-based catalysts as well as for developing drugs (Acc Chem Res (2012) p1345). The 'mother diamine' is also useful for making binol, monophos and binap analogs. The Chin group is also interested in using reversible covalent bonds for stereoselective recognition and L to D conversion of natural and non-natural amino acids (EJOC (2012) p229).

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