N,N-dibutyl-4-chlorobenzimidamide | 6936-38-5

• 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,N-dibutyl-4-chlorobenzimidamide
• 英文别名: N,N-dibutyl-4-chloro-benzamidine；N,N-Dibutyl-4-chlor-benzamidin；N,N-Dibutyl-4-chloro-benzenecarboximidamide；N,N-dibutyl-4-chlorobenzenecarboximidamide
• CAS: 6936-38-5
• 化学式: C₁₅H₂₃ClN₂
• 分子量: 266.814
• InChiKey: PKPNNFLLPTYWNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 二正丁胺 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.25h， 以98%的产率得到N,N-dibutyl-4-chlorobenzimidamide
  参考文献：
  名称：

  Synthesis of N,N-dialkylaminobenzonitriles and halo-(N,N-dialkyl)benzamidines by reaction of halobenzonitriles with lithium amides

  摘要：

  3- and 4-N,N-Dialkylaminobenzonitriles and 4-chloro-(N,N-dialkyl)benzamidines were isolated by reacting 4-chlorobenzonitrile with hindered lithium amides under thermodynamic (0 degrees C) and kinetic control conditions (-78 degrees C), respectively. As previously reported, a benzyne mechanism seems to be confirmed since N,N-dialkylaminobenzonitriles are formed. Only benzamidines were isolated in fair to high yields at both 0 degrees C and -78 degrees C with non-hindered lithium amides. Exploitation and mechanistic rationale of the reaction of different halobenzonitriles are also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.066

文献信息

• The Reaction of Halogenomagnesium Dialkylamides with Nitriles. The Preparation of N,N-Disubstituted Amidines
  作者：Emil Lorz、Richard Baltzly

  DOI：10.1021/ja01185a073

  日期：1948.5
• Synthesis of N,N-dialkylaminobenzonitriles and halo-(N,N-dialkyl)benzamidines by reaction of halobenzonitriles with lithium amides
  作者：Paola Vitale、Leonardo Di Nunno、Antonio Scilimati

  DOI：10.1016/j.tet.2011.06.066

  日期：2011.9

  3- and 4-N,N-Dialkylaminobenzonitriles and 4-chloro-(N,N-dialkyl)benzamidines were isolated by reacting 4-chlorobenzonitrile with hindered lithium amides under thermodynamic (0 degrees C) and kinetic control conditions (-78 degrees C), respectively. As previously reported, a benzyne mechanism seems to be confirmed since N,N-dialkylaminobenzonitriles are formed. Only benzamidines were isolated in fair to high yields at both 0 degrees C and -78 degrees C with non-hindered lithium amides. Exploitation and mechanistic rationale of the reaction of different halobenzonitriles are also reported. (C) 2011 Elsevier Ltd. All rights reserved.