N-(o-acetamidophenyl)phthalimide | 34442-95-0

• 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: N-(o-acetamidophenyl)phthalimide
• 英文别名: N-(2-acetylamino-phenyl)-phthalimide；N-(2-Acetylamino-phenyl)-phthalimid；N-(2-Acetamino-phenyl)-phthalimid；N-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetamide；N-[2-(1,3-dioxoisoindol-2-yl)phenyl]acetamide
• CAS: 34442-95-0
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: ORDHBAYDQASWED-UHFFFAOYSA-N

物化性质

• 熔点：
  201 °C
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(o-acetamidophenyl)phthalimide 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 5-acetyl-4b,5-dihydrobenzo[4,5]imidazo[2,1-a]isoindol-11-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：

  2-(2-硝基苯基)异吲哚-1,3-二酮 在 sodium hydrogensulfite 、 丙酮 作用下， 生成 N-(o-acetamidophenyl)phthalimide
  参考文献：
  名称：

  Rupe; Thiess, Chemische Berichte, 1909, vol. 42, p. 4290

  摘要：

  DOI：

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.
• Rupe; Thiess, Chemische Berichte, 1909, vol. 42, p. 4290
  作者：Rupe、Thiess

  DOI：——

  日期：——