5-phenyl-11(4bH)-oxoisoindolo[2,1-a]benzimidazole | 813468-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-phenyl-11(4bH)-oxoisoindolo[2,1-a]benzimidazole
• 英文别名: 5-phenyl-4b,5-dihydro-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-one；5-phenyl-4bH-isoindolo[2,3-a]benzimidazol-11-one
• CAS: 813468-94-9
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: RWORLGZIELYSER-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  481.1±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenyl-11(4bH)-oxoisoindolo[2,1-a]benzimidazole 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到4b,9-dihydro-15H-isoindolo[2,1-d]dibenzo[b,f]-1,4-diazepin-15-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
• 作为产物：
  描述：

  邻氨基二苯胺 在 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.08h， 生成 5-phenyl-11(4bH)-oxoisoindolo[2,1-a]benzimidazole
  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

• Palladium-catalyzed intramolecular C–N coupling: Facile synthesis of tetracyclic C(3)-aminoisoindolinones
  作者：H. Surya Prakash Rao、J. Prabhakaran

  DOI：10.1080/00397911.2022.2095647

  日期：2022.6.18

  isoindolinone and quinazoline motifs. The palladium-(II) catalyzed intramolecular Buchwald-Hartwig C–N coupling involving the C(3) amino and the N(2) 2-bromophenyl groups provided coveted heterocycles in excellent yields. The methodology is versatile, highly efficient, and has a wide scope for the synthesis of a range of medicinally important tetracyclic C(3)-aminoisoindolinones.

  摘要 在这里，我们报告了一种新的方法来获取包含稠合异吲哚啉酮和苯并咪唑啉或异吲哚啉酮和喹唑啉基序的四环杂环化合物。钯-(II) 催化的分子内 Buchwald-Hartwig C-N 偶联涉及 C(3) 氨基和 N(2) 2-溴苯基基团，以优异的收率提供了令人垂涎的杂环。该方法是通用的、高效的，并且具有广泛的合成一系列药用重要的四环 C(3)-氨基异吲哚啉酮的范围。
• 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.