N'-(2,6-dimethylphenyl)-N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester

• 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'-(2,6-dimethylphenyl)-N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester
• 英文别名: tert-butyl N-(2,6-dimethylanilino)-N-(2-methylphenyl)carbamate
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: RWWPTMJOUFHGBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(2,6-dimethylphenyl)-N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以72%的产率得到3,5,3'-trimethylbiphenyl-4,4'-diamine
  参考文献：
  名称：

  Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides

  摘要：

  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.

  DOI：

  10.1021/ol060451+
• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 、 N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester 在 palladium diacetate 、 caesium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以74%的产率得到N'-(2,6-dimethylphenyl)-N-o-tolyl-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Regioselective [5,5]-Sigmatropic Rearrangement Reactions of Aryl Hydrazides

  摘要：

  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.

  DOI：

  10.1021/ol060451+

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.