tert-butyl 2-(4-methoxyphenyl)-4-(2-phenylethynyl)-1H-pyrrole-1-carboxylate | 1159581-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl 2-(4-methoxyphenyl)-4-(2-phenylethynyl)-1H-pyrrole-1-carboxylate
• 英文别名: Tert-butyl 2-(4-methoxyphenyl)-4-(2-phenylethynyl)pyrrole-1-carboxylate；tert-butyl 2-(4-methoxyphenyl)-4-(2-phenylethynyl)pyrrole-1-carboxylate
• CAS: 1159581-73-3
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: RMKWGTWTSLJITD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 4-iodo-2-(4-methoxy-phenyl)-1H-pyrrole-1-carboxylate 、 苯乙炔 在 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以502 mg的产率得到tert-butyl 2-(4-methoxyphenyl)-4-(2-phenylethynyl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Three-Component Synthesis of N-Boc-4-iodopyrroles and Sequential One-Pot Alkynylation

  摘要：

  (Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted in a one-pot fashion to 2-substituted N-Boc-4-iodopyrroles. Upon addition of a further alkyne, another Sonogashira coupling can be carried out in a one-pot fashion. This sequentially Pd/Cu-catalyzed process represents a very mild and efficient entry to 2,4-disubstituted N-Boc-pyrroles.

  DOI：

  10.1021/ol900581a

文献信息

• Three-Component Synthesis of <i>N</i>-Boc-4-iodopyrroles and Sequential One-Pot Alkynylation
  作者：Eugen Merkul、Christina Boersch、Walter Frank、Thomas J. J. Müller

  DOI：10.1021/ol900581a

  日期：2009.6.4

  (Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted in a one-pot fashion to 2-substituted N-Boc-4-iodopyrroles. Upon addition of a further alkyne, another Sonogashira coupling can be carried out in a one-pot fashion. This sequentially Pd/Cu-catalyzed process represents a very mild and efficient entry to 2,4-disubstituted N-Boc-pyrroles.