1-benzyl-1,4,5,6-tetrahydrocyclopentpyrrole | 147329-69-9

• 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-benzyl-1,4,5,6-tetrahydrocyclopentpyrrole
• 英文别名: 1,4,5,6-tetrahydro-1-(phenylmethyl)cyclopenta[b]pyrrole；1-benzyl-5,6-dihydro-4H-cyclopenta[b]pyrrole
• CAS: 147329-69-9
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: IJPHLDXURCJUGO-UHFFFAOYSA-N

物化性质

• 沸点：
  320.0±11.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-benzyl-1,4,5,6-tetrahydrocyclopentpyrrole 在 aluminum oxide 作用下， 反应 2.0h， 生成 1-phenyl-3-(1-benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-2-propynone
  参考文献：
  名称：

  Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

  摘要：

  一种高效的方法已经开发出来，通过易得的酰基乙炔吡咯与硝酸胍的环缩合反应，合成了具有药用前景的吡咯-氨基嘧啶组合物（收率高达91%）。该反应在KOH/DMSO体系中在加热条件下进行（110-115°C，4小时）。在2-苯甲酰基乙炔吡咯的情况下，观察到形成的吡咯-氨基嘧啶作为N-（吡咯环的NH部分）和C-（氨基嘧啶的CH）亲核试剂意外地加到三键上。

  DOI：

  10.3390/molecules26061692
• 作为产物：
  描述：

  1-benzyl-1,4,5,6-tetrahydrocyclopentapyrrole-2-carboxylic acid 以99%的产率得到1-benzyl-1,4,5,6-tetrahydrocyclopentpyrrole
  参考文献：
  名称：

  Cyclopenta[b]indoles. Part 2. Model studies towards the tremorgenic mycotoxins

  摘要：

  The 7-bromocyclopenta[b]indole 3 has been converted into the hydroxybutenyl derivatives 5 and 6, and the tetrahydrofuranylidene derivative 8 in model studies towards the elaboration of paspalitrem and lolitrem type side chains. In a parallel approach, the cyclopentapyrrole 13 was converted into the fused alpha-pyrone 16 which acted as a pyrrole-2,3-quinodimethane, and underwent Diels-Alder reaction to give, after loss of carbon dioxide, the cyclopentaindoles 17-21.

  DOI：

  10.1039/p19950001131

文献信息

• [EN] SQUARYLIUM COMPOUNDS FOR USE IN DISPLAY DEVICES<br/>[FR] COMPOSÉS DE SQUARYLIUM POUR UTILISATION DANS DES DISPOSITIFS D'AFFICHAGE
  申请人：NITTO DENKO CORP

  公开号：WO2019108544A3

  公开（公告）日：2019-07-11
• Synthesis of tri- and tetramethylene[b]pyrrole derivatives from 2-(1-ethoxy-2-bromoethyl)cycloalkanones
  作者：A. Azzuz、V. L. Sorokin、O. G. Kulinkovich

  DOI：10.1007/bf00529474

  日期：1992.1
• SQUARYLIUM COMPOUNDS FOR USE IN DISPLAY DEVICES
  申请人：Nitto Denko Corporation

  公开号：EP3717572A2

  公开（公告）日：2020-10-07
• Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
  作者：Olga V. Petrova、Arsalan B. Budaev、Elena F. Sagitova、Igor A. Ushakov、Lyubov N. Sobenina、Andrey V. Ivanov、Boris A. Trofimov

  DOI：10.3390/molecules26061692

  日期：——

  An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

  一种高效的方法已经开发出来，通过易得的酰基乙炔吡咯与硝酸胍的环缩合反应，合成了具有药用前景的吡咯-氨基嘧啶组合物（收率高达91%）。该反应在KOH/DMSO体系中在加热条件下进行（110-115°C，4小时）。在2-苯甲酰基乙炔吡咯的情况下，观察到形成的吡咯-氨基嘧啶作为N-（吡咯环的NH部分）和C-（氨基嘧啶的CH）亲核试剂意外地加到三键上。
• Cyclopenta[b]indoles. Part 2. Model studies towards the tremorgenic mycotoxins
  作者：Carrie-Ann Harrison、P. Mark Jackson、Christopher J. Moody、Jonathan M. J. Williams

  DOI：10.1039/p19950001131

  日期：——

  The 7-bromocyclopenta[b]indole 3 has been converted into the hydroxybutenyl derivatives 5 and 6, and the tetrahydrofuranylidene derivative 8 in model studies towards the elaboration of paspalitrem and lolitrem type side chains. In a parallel approach, the cyclopentapyrrole 13 was converted into the fused alpha-pyrone 16 which acted as a pyrrole-2,3-quinodimethane, and underwent Diels-Alder reaction to give, after loss of carbon dioxide, the cyclopentaindoles 17-21.