1--3-methylpyrrolo<1,2-a>azepane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: 1--3-methylpyrrolo<1,2-a>azepane
• 英文别名: furan-2-yl-(3-methyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepin-1-yl)methanimine
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: AWLUXHGLCUWIJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1--3-methylpyrrolo<1,2-a>azepane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以72%的产率得到1--3-methylpyrrolo<1,2-a>azepane
  参考文献：
  名称：

  An Efficient Approach to Pyrroles and N-Bridgehead Pyrroles by Propargylation/Cycloamination of 4-Amino-1-azabutadiene Derivatives

  摘要：

  The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.

  DOI：

  10.1021/jo951887y
• 作为产物：
  描述：

  2-methyl-4,5,6,7-tetrahydro-3H-azepine 、 2-氰基呋喃 、 3-溴丙炔 在 lithium diisopropyl amide 作用下， 生成 1--3-methylpyrrolo<1,2-a>azepane
  参考文献：
  名称：

  An Efficient Approach to Pyrroles and N-Bridgehead Pyrroles by Propargylation/Cycloamination of 4-Amino-1-azabutadiene Derivatives

  摘要：

  The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.

  DOI：

  10.1021/jo951887y

文献信息

• An Efficient Approach to Pyrroles and <i>N</i><b>-Bridgehead Pyrroles by Propargylation/Cycloamination of 4-Amino-1-azabutadiene Derivatives</b>
  作者：José Barluenga、Miguel Tomás、Vladimir Kouznetsov、Angel Suárez-Sobrino、Eduardo Rubio

  DOI：10.1021/jo951887y

  日期：1996.1.1

  The thermal cycloamination of several propargyl-substituted 4-amino-1-azabutadienes 2 leading to 3-functionalized pyrroles 4-6 is described. Derivatives of pyrrolizidines 9 and indolizidines and azaazulenes 11-13 are synthesized directly from cyclic imines 7 and 10, respectively, in a multistep process that involves metalation with LDA, addition of a nitrile, carbanion trapping with propargyl bromide, and cycloamination. In all cases the more substituted imine nitrogen is involved in the cyclization reaction; such an experimental finding is supported by theoretical calculations.