3-deutero-4-chlorobenzonitrile | 1332874-34-6

• 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: 3-deutero-4-chlorobenzonitrile
• CAS: 1332874-34-6
• 化学式: C₇H₄ClN
• 分子量: 138.561
• InChiKey: GJNGXPDXRVXSEH-WFVSFCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶 、 邻氯苯腈 在 正丁基锂 、 氘代甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成 3-deutero-4-chlorobenzonitrile 、 2-deutero-4-chlorobenzonitrile
  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

• 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.