(2-fluoro-pyrrolo[2,1-a]isoquinolin-3-yl)phenyl-methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-fluoro-pyrrolo[2,1-a]isoquinolin-3-yl)phenyl-methanone
• 英文别名: (2-Fluoropyrrolo[2,1-a]isoquinolin-3-yl)-phenylmethanone
• 化学式: C₁₉H₁₂FNO
• 分子量: 289.309
• InChiKey: CVZAQSIIHWGZJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1,1,2-四氟乙烷 、 2-phenacylisoquinolinium bromide 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到(2-fluoro-pyrrolo[2,1-a]isoquinolin-3-yl)phenyl-methanone
  参考文献：
  名称：

  A facile synthetic method for 2-fluoroindolizines from 1-chloro-2,2,2-trifluoroethane (HCFC-133a) and 1,1,1,2-tetrafluoroethane (HFC-134a)

  摘要：

  In the presence of KOH and Et3N. pyridinium and isoquinolinium N-ylides generated in situ from their bromides react with 1-chloro-2,2,2-trifluoroethane (HCFC-133a. bp 6 degreesC) or 1,1,1,2-tetrafluoroethane (HFC-134a, bp -27 degreesC) to give the corresponding 2-fluoroindolizines via 1,3-dipolar [3 divided by 2] cycloaddition at 80-100 degreesC in DMSO at atmospheric pressure in normal glassware. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00055-1

文献信息

• Synthesis of monofluorinated indolizines and their derivatives by the 1,3-dipolar reaction of N-ylides with fluorinated vinyl tosylates
  作者：Xiang Fang、Yong-Ming Wu、Juan Deng、Shao-Wu Wang

  DOI：10.1016/j.tet.2004.04.012

  日期：2004.6

  Monofluorinated indolizines 4, benzo[d]indolizines 7 and 4H-pyrrolo[1,2-a]benzimidazoles 8 were synthesized in moderate yields by 1,3-dipolar reaction between fluorinated vinyl tosylates 2a and N-ylides of pyridinium, isoquinolinium and benzimidazolinium, generated in situ from their halides salts. When the same N-ylides were allowed to react with 2,3,3-trifluoro-1-propenyl tosylate 2b, the unexpected product formylated indolizines and their derivatives 9 were obtained. The reaction mechanism is also proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• A facile synthetic method for 2-fluoroindolizines from 1-chloro-2,2,2-trifluoroethane (HCFC-133a) and 1,1,1,2-tetrafluoroethane (HFC-134a)
  作者：Kai Wu、Qing-Yun Chen

  DOI：10.1016/s0022-1139(03)00055-1

  日期：2003.8

  In the presence of KOH and Et3N. pyridinium and isoquinolinium N-ylides generated in situ from their bromides react with 1-chloro-2,2,2-trifluoroethane (HCFC-133a. bp 6 degreesC) or 1,1,1,2-tetrafluoroethane (HFC-134a, bp -27 degreesC) to give the corresponding 2-fluoroindolizines via 1,3-dipolar [3 divided by 2] cycloaddition at 80-100 degreesC in DMSO at atmospheric pressure in normal glassware. (C) 2003 Elsevier Science B.V. All rights reserved.