1-异丙烯基-4,5,6,7-四氢-1H-吲哚 | 634892-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-异丙烯基-4,5,6,7-四氢-1H-吲哚
• 英文名称: 1-isopropenyl-4,5,6,7-tetrahydro-1H-indole
• 英文别名: 1-isopropenyl-4,5,6,7-tetrahydroindole；N-isopropenyl-4,5,6,7-tetrahydroindole；1-(Prop-1-en-2-yl)-4,5,6,7-tetrahydro-1H-indole；1-prop-1-en-2-yl-4,5,6,7-tetrahydroindole
• CAS: 634892-64-1
• 化学式: C₁₁H₁₅N
• mdl: MFCD18809056
• 分子量: 161.247
• InChiKey: QQXBOCHHIINTLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 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：

  三甲基氯硅烷 、 1-异丙烯基-4,5,6,7-四氢-1H-吲哚 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以68%的产率得到1-[3-(trimethylsilyl)prop-1-en-2-yl]-4,5,6,7-tetrahydro-1H-indole
  参考文献：
  名称：

  Towards Rare-Functionalized N-Alkenyl-1H-pyrroles via Regioselectively Metalated N-Isopropenyl-1H-pyrroles

  摘要：

  摘要：研究了使用超碱对N-异丙烯基-1H-吡咯进行去质子化金属化反应，然后用各种电子亲和试剂捕捉的方法，作为1H-吡咯区域选择性官能化的有效工具。

  DOI：

  10.1055/a-1736-4200
• 作为产物：
  描述：

  4,5,6,7-四氢吲哚 、 丙炔 生成 1-异丙烯基-4,5,6,7-四氢-1H-吲哚
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070428007030116

文献信息

• 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%。
• ——
  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.
• 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.
• Towards Rare-Functionalized N-Alkenyl-1H-pyrroles via Regioselectively Metalated N-Isopropenyl-1H-pyrroles
  作者：Ol'ga A. Tarasova、Boris A. Trofimov、Marina A. Maximova、Alexander I. Albanov、Nina A. Nedolya

  DOI：10.1055/a-1736-4200

  日期：2022.5

  Deprotonative metalation of N-isopropenyl-1H-pyrroles with superbases followed by trapping with a variety of electrophiles was studied as an effective tool for the regioselective functionalization of 1H-pyrroles.

  摘要：研究了使用超碱对N-异丙烯基-1H-吡咯进行去质子化金属化反应，然后用各种电子亲和试剂捕捉的方法，作为1H-吡咯区域选择性官能化的有效工具。

表征谱图