1-isopropenyl-2-phenyl-1H-pyrrole | 634892-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-isopropenyl-2-phenyl-1H-pyrrole
• 英文别名: 1-isopropenyl-2-phenylpyrrole；N-isopropenyl-2-phenylpyrrole；2-phenyl-1-prop-1-en-2-ylpyrrole
• CAS: 634892-65-2
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: SEPTYFGCUQVFCF-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 5 Torr)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  3-溴-1-苯基丙-2-炔-1-酮 、 1-isopropenyl-2-phenyl-1H-pyrrole 在 aluminum oxide 作用下， 反应 1.0h， 以68%的产率得到2-(2-benzoylethynyl)-1-isopropenyl-5-phenylpyrrole
  参考文献：
  名称：

  Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al₂O₃: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles

  摘要：

  1-乙烯基-和1-异丙烯基吡咯很容易（环境温度）与Al2O3上的酰基溴乙炔发生交叉偶联反应，从而区域选择性地提供2-(2-酰基乙炔基)-1-乙烯基-和2-(2-酰基乙炔基)-1-异丙烯基吡咯产率 39-70%。

  DOI：

  10.1055/s-2007-965884
• 作为产物：
  描述：

  2-苯基-吡咯 、 丙二烯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以28%的产率得到1-isopropenyl-2-phenyl-1H-pyrrole
  参考文献：
  名称：

  摘要：

  A number of previously unknown N-isopropenyl-substituted pyrroles, indoles, and di- and -triazoles were synthesized in 20-86% yield by reaction of the corresponding azole with an equilibrium mixture of propyne with allene or pure propyne and allene in the system KOH-DMSO (105-145degreesC, 5-15 h, atmospheric or elevated pressure). The reaction is regioselective. The electronic and steric structure and the degree of conjugation between the exocyclic double bond and the azole ring are discussed on the basis of the H-1 and C-13 NMR spectra. Almost complete absence of p-pi conjugation in alpha,alpha'-disubstitutecl N-isopropenylazoles have been found.

  DOI：

  10.1023/a:1025502016921

文献信息

• Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data
  作者：A. V. Afonin、I. A. Ushakov、D. E. Simonenko、O. A. Tarasova、M. A. Maksimova、B. A. Trofimov

  DOI：10.1134/s1070428007030116

  日期：2007.3

  According to the H-1 and C-13 NMR data, 1-isopropenylpyrroles are characterized by larger dihedral angles between the heteroring and exocyclic double bond planes, as compared to isostructural 1-vinylpyrroles, due to steric effect of the alpha-methyl group in the propenyl fragment. As a result, p-pi conjugation with the propenyl group is weaker than with the vinyl group. The propenyl group in 1-isopropenylpyrrole having no other substituents in the heteroring is forced out from the heteroring plane, while the 1-vinylpyrrole molecule is planar. If substituents are present in positions 2 and 5 of the pyrrole ring, the propenyl group on the nitrogen atom becomes orthogonal with respect to the pyrrole ring plane, so that no p-pi conjugation is possible. The steric structures of (E)-1-(prop-1-en-1-yl)pyrrole and (Z)-1-(prop-l-en-l-yl)pyrrole are different: the propenyl group in the former is turned relative to the heteroring plane, while the latter molecule is planar.
• ——
  作者：B. A. Trofimov、O. A. Tarasova、M. A. Shemetova、A. V. Afonin、L. V. Klyba、L. V. Baikalova、A. I. Mikhaleva

  DOI：10.1023/a:1025502016921

  日期：——

  A number of previously unknown N-isopropenyl-substituted pyrroles, indoles, and di- and -triazoles were synthesized in 20-86% yield by reaction of the corresponding azole with an equilibrium mixture of propyne with allene or pure propyne and allene in the system KOH-DMSO (105-145degreesC, 5-15 h, atmospheric or elevated pressure). The reaction is regioselective. The electronic and steric structure and the degree of conjugation between the exocyclic double bond and the azole ring are discussed on the basis of the H-1 and C-13 NMR spectra. Almost complete absence of p-pi conjugation in alpha,alpha'-disubstitutecl N-isopropenylazoles have been found.
• Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al₂O₃: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles
  作者：B. Trofimov、L. Sobenina、Z. Stepanova、I. Ushakov、O. Petrova、O. Tarasova、K. Volkova、A. Mikhaleva

  DOI：10.1055/s-2007-965884

  日期：2007.2

  1-Vinyl- and 1-isopropenylpyrroles enter readily (ambient temperature) into cross-coupling reaction with acylbromoacet­ylenes on Al2O3 to furnish regioselectively 2-(2-acylethynyl)-1-vinyl- and 2-(2-acylethynyl)-1-isopropenylpyrroles in 39-70% yield.

  1-乙烯基-和1-异丙烯基吡咯很容易（环境温度）与Al2O3上的酰基溴乙炔发生交叉偶联反应，从而区域选择性地提供2-(2-酰基乙炔基)-1-乙烯基-和2-(2-酰基乙炔基)-1-异丙烯基吡咯产率 39-70%。