2,3-二甲基-1-乙烯基-1H-吡咯 | 55847-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,3-二甲基-1-乙烯基-1H-吡咯
• 英文名称: 2,3-dimethyl-1-vinyl-1H-pyrrole
• 英文别名: 2,3-dimethyl-1-vinyl-pyrrole；2,3-Dimethyl-1-vinylpyrrole；1-ethenyl-2,3-dimethylpyrrole
• CAS: 55847-29-5
• 化学式: C₈H₁₁N
• mdl: MFCD01099318
• 分子量: 121.182
• InChiKey: QCYQBSQGDYKGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1-乙烯基-1H-吡咯 、 乙醇 在 四氯化碳 、 偶氮二异丁腈 作用下， 反应 0.5h， 以60%的产率得到1-(1-Ethoxyethyl)-2,3-dimethylpyrrole
  参考文献：
  名称：

  Korostova, S. E.; Mikhaleva, A. I.; Trofimov, B. A., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 460 - 462

  摘要：

  DOI：
• 作为产物：
  描述：

  丁酮肟 、 乙炔 生成 2,3-二甲基-1-乙烯基-1H-吡咯
  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

• Trofimov, B. A.; Oleinikova, E. B.; Sigalov, M. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 366 - 370
  作者：Trofimov, B. A.、Oleinikova, E. B.、Sigalov, M. V.、Skvortsov, Yu. M.、Mikhaleva, A. I.

  DOI：——

  日期：——
• Shmidt; Vladimirova; Dmitrieva, Russian Journal of General Chemistry, 1996, vol. 66, # 9, p. 1497 - 1500
  作者：Shmidt、Vladimirova、Dmitrieva、Zinchenko

  DOI：——

  日期：——
• Pyrroles from ketoximes and acetylene. 29. Synthesis of alkylpyrroles from dialkylketoximes and dichloroethane by reaction with KOH-DMSO
  作者：B. A. Trofimov、A. I. Mikhaleva、A. N. Vasil'ev、S. E. Korostova、S. G. Shevchenko

  DOI：10.1007/bf00505898

  日期：1985.1
• Regioselective ?-arylation ofN-vinylpyrroles by the Heck reaction
  作者：A. F. Shmidt、T. A. Vladimirova、E. Yu. Shmidt、T. V. Dmitrieva

  DOI：10.1007/bf00698522

  日期：1995.4
• Selective synthesis of 1-vinylpyrroles directly from ketones and acetylene: Modification of trofimov reaction
  作者：A. I. Mikhaleva、E. Yu. Shmidt、A. V. Ivanov、A. M. Vasil’tsov、E. Yu. Senotrusova、N. I. Protsuk

  DOI：10.1134/s1070428007020133

  日期：2007.2

  Consecutive treatment of ketones with a system NH2OH center dot HCl-NaHCO3-DMSO and acetylene excess in the presence of KOH (100-120 degrees C, initial acetylene pressure 12-15 at) led to a selective formation of 2- and 2,3-substituted 1-vinylpyrroles in 51-79% yields. Ketones of aliphatic, cycloaliphatic, aromatic, heteroaromatic, and tetrahydronaphthalene series were involved into the reaction.