2,3-Dihydro-1-vinyl-N-methyl-1H-isoindole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,3-Dihydro-1-vinyl-N-methyl-1H-isoindole
• 英文别名: 1-Ethenyl-2-methyl-1,3-dihydroisoindole
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: JPBISVMEXPJBAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-Dihydro-1-vinyl-N-methyl-1H-isoindole 在 四(三苯基膦)钯 乙酸烯丙酯 作用下， 以 氘代乙腈 为溶剂， 反应 48.0h， 以96%的产率得到2,3-dihydro-2-methyl-1H-2-benzazepine
  参考文献：
  名称：

  Heterocyclization, deprotection and isomerization in an intramolecular palladium-catalysed tertiary amine–allyl coupling reaction

  摘要：

  N-Methyl-N-allyl-2-(1-acetoxyallyl)benzylamine reacts in the presence of tetrakis(triphenylphosphine)palladium to afford a mixture of an isoindole, a 2-benzazepine and allyl acetate; the likely reaction pathway involves a multistep procedure whereby each Pd atom is implicated at least four times, the formation of the isoindole occuring first, followed by an isomerisation to the benzazepine derivative.

  DOI：

  10.1039/cc9960002257
• 作为产物：
  描述：

  N-Methyl-N-allyl-2-(1-acetoxyallyl)benzylamine 在 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 乙酸烯丙酯 、 2,3-dihydro-2-methyl-1H-2-benzazepine 、 2,3-Dihydro-1-vinyl-N-methyl-1H-isoindole
  参考文献：
  名称：

  Heterocyclization, deprotection and isomerization in an intramolecular palladium-catalysed tertiary amine–allyl coupling reaction

  摘要：

  N-Methyl-N-allyl-2-(1-acetoxyallyl)benzylamine reacts in the presence of tetrakis(triphenylphosphine)palladium to afford a mixture of an isoindole, a 2-benzazepine and allyl acetate; the likely reaction pathway involves a multistep procedure whereby each Pd atom is implicated at least four times, the formation of the isoindole occuring first, followed by an isomerisation to the benzazepine derivative.

  DOI：

  10.1039/cc9960002257

文献信息

• ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Electronics Co., Ltd.

  公开号：EP3000815B1

  公开（公告）日：2017-07-19
• Heterocyclization, deprotection and isomerization in an intramolecular palladium-catalysed tertiary amine–allyl coupling reaction
  作者：Mary Grellier、Michel Pfeffer

  DOI：10.1039/cc9960002257

  日期：——

  N-Methyl-N-allyl-2-(1-acetoxyallyl)benzylamine reacts in the presence of tetrakis(triphenylphosphine)palladium to afford a mixture of an isoindole, a 2-benzazepine and allyl acetate; the likely reaction pathway involves a multistep procedure whereby each Pd atom is implicated at least four times, the formation of the isoindole occuring first, followed by an isomerisation to the benzazepine derivative.