N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester | 681815-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
• 英文别名: tert-butyl N-[3,5-bis[2-(2-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]anilino]-N-(2-methoxyphenyl)carbamate
• CAS: 681815-56-5
• 化学式: C₄₂H₅₄N₆O₉
• 分子量: 786.926
• InChiKey: MMWDRRJTMCERFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  57
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester 在 copper(l) iodide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以63%的产率得到
  参考文献：
  名称：

  Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations

  摘要：

  A series of novel 1,3,5-tris-azobenzenes were prepared from 1,3,5-trihalobenzene via Pd-catalyzed couplings of N-Boc aryl hydrazines and subsequent Cu(I)-mediated direct oxidations. The oxidation of tris-arylhydrazide provided the azobenzene as a mixture of all four of the possible E/Z-isomers; [E,E,E]-, [E,E,Z]-, [E,Z,Z]-, and [Z,Z,Z]-1,3,5-tris-azobenzenes. A slow removal of the solvent in the dark transformed the isomers into the all-trans, [E,E,E]-isomer.

  DOI：

  10.1021/jo035720d
• 作为产物：
  描述：

  1,3,5-三溴苯 、 N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester 在 palladium diacetate 、 三叔丁基膦 caesium carbonate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.5h， 以99%的产率得到N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations

  摘要：

  A series of novel 1,3,5-tris-azobenzenes were prepared from 1,3,5-trihalobenzene via Pd-catalyzed couplings of N-Boc aryl hydrazines and subsequent Cu(I)-mediated direct oxidations. The oxidation of tris-arylhydrazide provided the azobenzene as a mixture of all four of the possible E/Z-isomers; [E,E,E]-, [E,E,Z]-, [E,Z,Z]-, and [Z,Z,Z]-1,3,5-tris-azobenzenes. A slow removal of the solvent in the dark transformed the isomers into the all-trans, [E,E,E]-isomer.

  DOI：

  10.1021/jo035720d

文献信息

• Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides
  作者：Hong-Min Kang、Young-Kwan Lim、In-Jee Shin、Hee-Yeon Kim、Cheon-Gyu Cho

  DOI：10.1021/ol060451+

  日期：2006.5.1

  N,N'-Aryl hydrazides with substituents at the ortho or meta positions undergo highly regioselective [5,5]-sigmatropic rearrangement reactions to furnish benzidines in good to excellent isolated yields. The presence of single substituent at either the ortho or meta position provides sufficient bias, effectively suppressing the formation of diphenylene, the major byproduct of the conventional benzidine rearrangement reaction.
• Synthesis of Novel 1,3,5-Tris(arylazo)benzenes via Pd-Catalyzed Couplings and Cu(I)-Mediated Direct Oxidations
  作者：Young-Kwan Lim、Sunju Choi、Kyung Bae Park、Cheon-Gyu Cho

  DOI：10.1021/jo035720d

  日期：2004.4.1

  A series of novel 1,3,5-tris-azobenzenes were prepared from 1,3,5-trihalobenzene via Pd-catalyzed couplings of N-Boc aryl hydrazines and subsequent Cu(I)-mediated direct oxidations. The oxidation of tris-arylhydrazide provided the azobenzene as a mixture of all four of the possible E/Z-isomers; [E,E,E]-, [E,E,Z]-, [E,Z,Z]-, and [Z,Z,Z]-1,3,5-tris-azobenzenes. A slow removal of the solvent in the dark transformed the isomers into the all-trans, [E,E,E]-isomer.