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Merck
CN

685860

(1R,2R)-1,2-双(2-羟苯基)乙烯二胺

95% (HPLC)

别名:

(1R,2R)-1,2-双(2-羟苯基)-1,2-乙二胺, (R,R) -1,2-双(2-羟基苯基)亚乙基二胺, (R,R) -1,2-双(2-羟苯基)-1,2-乙二胺, (R,R) -1,2-双(2-羟苯基)乙二胺

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关于此项目

经验公式（希尔记法）:
C14H16N2O2
化学文摘社编号:
870991-70-1
分子量:
244.29
NACRES:
NA.22
PubChem Substance ID:
24885846
UNSPSC Code:
12352116
MDL number:
MFCD09751760

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产品名称

(1R,2R)-1,2-双(2-羟苯基)乙烯二胺, 95% (HPLC)

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-/m1/s1

SMILES string

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

InChI key

MRNPLGLZBUDMRE-ZIAGYGMSSA-N

assay

95% (HPLC)

form

powder

optical activity

[α]22/D +62°, c = 1% in chloroform

mp

157-163 °C

functional group

amine

Application

(1R,2R)-1,2-双(2-羟苯基)乙烯二胺可用作合成以下化合物的前体：
  • 对映体纯反式-3-芳基哌嗪-2-羧酸衍生物，通过氮杂-Cope重排(DCR)
  • 4,4′-(1,2-二铵乙烷-1,2-二基）二苯甲酸盐三水合物，通过对苯二酸处理。

General description

(1R, 2R)-1,2-双(2-羟苯基)乙烯二胺或称(R, R)-1,2-双(2-羟苯基)-1,2-二氨基乙烷（HPEN）常用于对映体纯化合物的立体选择性合成。

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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, Faceshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCP5623
MKCM7937
MKCL7014
MKCK3589
MKCG7386

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Short synthesis of enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement
Kwon SH, et al.
Organic Letters, 14(14) (2012)
4, 4?-(1, 2-Diazaniumylethane-1, 2-diyl) dibenzoate trihydrate
Numata T, et al.
IUCrData, 1(2), x160252-x160252 (2016)
Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994.
Kim, Miji and Kim, Hyeseung and Kim, Hyunwoo and Chin, Jik
The Journal of Organic Chemistry, 82(23), 12050-12058 (2017)
An efficient synthesis of chiral diamines with rigid backbones: Application in enantioselective michael addition of malonates to nitroalkenes.
Zhu, Qiming and Huang, Hanmin and Shi, Dengjian and Shen, Zhiqiang and Xia, Chungu
Organic Letters, 11(20), 4536-4539 (2009)
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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