4-chloro-1-isopropyl-2-phenylpyrrole | 850641-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-chloro-1-isopropyl-2-phenylpyrrole
• 英文别名: 4-Chloro-2-phenyl-1-propan-2-ylpyrrole
• CAS: 850641-94-0
• 化学式: C₁₃H₁₄ClN
• 分子量: 219.714
• InChiKey: NOTGKLGVXUINBL-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  311.3±22.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  氯甲酸甲酯 、 4-chloro-1-isopropyl-2-phenylpyrrole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以77%的产率得到methyl (3-chloro-1-isopropyl-5-phenylpyrrol-2-yl)carboxylate
  参考文献：
  名称：

  Synthesis of 2-aryl-4-chloropyrroles via ring expansion of 2-aryl-1-chlorocyclopropanecarbaldehydes

  摘要：

  An efficient electrophile-induced ring opening of 2-aryl-1-chlorocyclopropanecarbaldehydes is described towards halogenated butanals, which were converted to the corresponding imines. These alpha,alpha,gamma-trichloroimines proved to be good substrates for a nucleophile-induced ring closure towards 2-pyrrolines as versatile synthons for the synthesis of pyrroles bearing physiologically interesting substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.087
• 作为产物：
  描述：

  3-chloro-2-cyano-1-isopropyl-5-phenyl-2-pyrroline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到4-chloro-1-isopropyl-2-phenylpyrrole
  参考文献：
  名称：

  Synthesis of 2-aryl-4-chloropyrroles via ring expansion of 2-aryl-1-chlorocyclopropanecarbaldehydes

  摘要：

  An efficient electrophile-induced ring opening of 2-aryl-1-chlorocyclopropanecarbaldehydes is described towards halogenated butanals, which were converted to the corresponding imines. These alpha,alpha,gamma-trichloroimines proved to be good substrates for a nucleophile-induced ring closure towards 2-pyrrolines as versatile synthons for the synthesis of pyrroles bearing physiologically interesting substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.087

文献信息

• Synthesis of 2-aryl-4-chloropyrroles via ring expansion of 2-aryl-1-chlorocyclopropanecarbaldehydes
  作者：Guido Verniest、Sven Claessens、Filip Bombeke、Tinneke Van Thienen、Norbert De Kimpe

  DOI：10.1016/j.tet.2005.01.087

  日期：2005.3

  An efficient electrophile-induced ring opening of 2-aryl-1-chlorocyclopropanecarbaldehydes is described towards halogenated butanals, which were converted to the corresponding imines. These alpha,alpha,gamma-trichloroimines proved to be good substrates for a nucleophile-induced ring closure towards 2-pyrrolines as versatile synthons for the synthesis of pyrroles bearing physiologically interesting substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.