2-(2,2-dimethylcyclopropyl)-N4,N4-dimethylbenzene-1,4-diamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2,2-dimethylcyclopropyl)-N4,N4-dimethylbenzene-1,4-diamine
• 英文别名: 2-(2,2-dimethylcyclopropyl)-4-N,4-N-dimethylbenzene-1,4-diamine
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: WVIWJRKEJGTEDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氯-2,2-二甲基环丙基苯基亚砜 、 N,N-二甲基-对苯二胺 在 正丁基锂 、 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到2-(2,2-dimethylcyclopropyl)-N4,N4-dimethylbenzene-1,4-diamine
  参考文献：
  名称：

  The first example of direct cyclopropylation of arylamines at the 2-position with magnesium cyclopropylidenes

  摘要：

  Treatment of magnesium cyclopropylidenes, which were generated from 1-chlorocyclopropyl phenyl sulfoxides with isopropylmagnesium chloride in THF at -78 degrees C, with N-lithio arylamines gave arylamines cyclopropylated at the 2-position in moderate to good yields. Use of the magnesium cyclopropylidenes having at least one substituent was found to be essential to this cyclopropylation. This procedure offers a novel synthesis of arylamines having a cyclopropane ring at the 2-position directly from arylamines. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.122

文献信息

• Cyclopropylation of arylamines at the 2-position with cyclopropylmagnesium carbenoids
  作者：Yukie Yamada、Mirai Mizuno、Shinobu Nagamoto、Tsuyoshi Satoh

  DOI：10.1016/j.tet.2009.09.096

  日期：2009.11

  Direct cyclopropylation of arylamines at the 2-position with 1-chlorocyclopropyl phenyl sulfoxides was achieved. The reaction of N-lithio arylamines with cyclopropylinagnesium carbenoids, which are generated from 1-chlorocyclopropyl phenyl sulfoxides with i-PrMgCl via the sulfoxide-magnesium exchange reaction, is the key of this procedure, This method offers an unprecedented way for the synthesis of arylamines having a cyclopropane ring at the 2-position directly from arylamines. (C) 2009 Elsevier Ltd. All rights reserved.