5,6,7,13b-tetrahydroisoindolo[2,1-d][1,4]benzodiazepin-9-one | 36271-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 5,6,7,13b-tetrahydroisoindolo[2,1-d][1,4]benzodiazepin-9-one
• 英文别名: 5,6,7,13b-tetrahydro-benzo[5,6][1,4]diazepino[7,1-a]isoindol-9-one；8,11-Diazatetracyclo[9.7.0.02,7.013,18]octadeca-2,4,6,13,15,17-hexaen-12-one
• CAS: 36271-36-0
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: METVQTCJVWQRAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-(苯基氨基)乙基)邻苯二甲酰亚胺 在 sodium tetrahydroborate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.08h， 生成 5,6,7,13b-tetrahydroisoindolo[2,1-d][1,4]benzodiazepin-9-one
  参考文献：
  名称：

  Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation

  摘要：

  Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable alpha,beta-diamine IV (or corresponding (beta-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular alpha-aza-amidoalkylation of the N-acyliminium species. Furthermore, when R-2 is an aromatic moiety a competing alpha-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.107

文献信息

• Kinetic versus thermodynamic access to imidazoisoindolones, benzimidazoisoindolones, and [1,4]diazepinoisoindolones: intramolecular nitrogen and π-aromatic trapping of N-acyliminium cation
  作者：Armelle Cul、Adam Daïch、Bernard Decroix、Gérard Sanz、Luc Van Hijfte

  DOI：10.1016/j.tet.2004.07.107

  日期：2004.11

  Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable alpha,beta-diamine IV (or corresponding (beta-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular alpha-aza-amidoalkylation of the N-acyliminium species. Furthermore, when R-2 is an aromatic moiety a competing alpha-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed. (C) 2004 Elsevier Ltd. All rights reserved.