5,6-dihydro-2-methylpyrrolo[2,1-a]isoindolin-3(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5,6-dihydro-2-methylpyrrolo[2,1-a]isoindolin-3(2H)-one
• 英文别名: 2-methyl-5,6-dihydro-2H-pyrrolo[2,1-a]isoquinolin-3-one
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: ZCUPLWTVBOSFKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  柠康酸酐 在 bismuth(lll) trifluoromethanesulfonate 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.0h， 生成 5,6-dihydro-2-methylpyrrolo[2,1-a]isoindolin-3(2H)-one
  参考文献：
  名称：

  Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst

  摘要：

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

  DOI：

  10.1021/jo062077x

文献信息

• Intermolecular and Intramolecular α-Amidoalkylation Reactions Using Bismuth Triflate as the Catalyst
  作者：Frédéric Pin、Sébastien Comesse、Bernard Garrigues、Štefan Marchalín、Adam Daïch

  DOI：10.1021/jo062077x

  日期：2007.2.1

  Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).