N-butyl-N'-(S)-α-methylbenzyl-1,2-diaminobenzene | 291545-07-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-butyl-N'-(S)-α-methylbenzyl-1,2-diaminobenzene
• 英文别名: 1-N-butyl-2-N-[(1S)-1-phenylethyl]benzene-1,2-diamine
• CAS: 291545-07-8
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: ATCIDHFDSZDLCO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butyl-N'-(S)-α-methylbenzyl-1,2-diaminobenzene 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 1-(S)-α-methylbenzyl-2-phenyl-3-n-butyl-benzimidazolium chloride
  参考文献：
  名称：

  A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence

  摘要：

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.

  DOI：

  10.1021/ol016254m
• 作为产物：
  描述：

  1,2-二溴苯 在 tris(dibenzylideneacetone)dipalladium (0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 N-butyl-N'-(S)-α-methylbenzyl-1,2-diaminobenzene
  参考文献：
  名称：

  Synthesis of chiral N,N′-disubstituted 1,2-benzenediamines from o-dibromobenzene

  摘要：

  Palladium-catalyzed amination of o-dibromobenzene provided chiral N,N'-disubstituted 1,2-benzenediamines in good to excellent yields. The amination was executed stepwise and in one pot to give unsymmetrically and symmetrically substituted 1,2-benzenediamines. Incorporation of chiral primary amines was possible without racemization using catalytic Pd(2)dba(3)-BINAP. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00124-5

文献信息

• A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence
  作者：Felix M. Rivas、Uzma Riaz、Anthony Giessert、Jason A. Smulik、Steven T. Diver

  DOI：10.1021/ol016254m

  日期：2001.8.1

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.
• Synthesis of chiral N,N′-disubstituted 1,2-benzenediamines from o-dibromobenzene
  作者：Felix M Rivas、Uzma Riaz、Steven T Diver

  DOI：10.1016/s0957-4166(00)00124-5

  日期：2000.5

  Palladium-catalyzed amination of o-dibromobenzene provided chiral N,N'-disubstituted 1,2-benzenediamines in good to excellent yields. The amination was executed stepwise and in one pot to give unsymmetrically and symmetrically substituted 1,2-benzenediamines. Incorporation of chiral primary amines was possible without racemization using catalytic Pd(2)dba(3)-BINAP. (C) 2000 Elsevier Science Ltd. All rights reserved.