2,3-dihydro-3-hydroxy-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one | 189949-65-3

• 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-3-hydroxy-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one
• 英文别名: methyl 2-[(1-hydroxy-3-oxo-1H-isoindol-2-yl)methyl]benzoate
• CAS: 189949-65-3
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: SWRQSYOETFAPQG-UHFFFAOYSA-N

物化性质

• 沸点：
  523.9±50.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-3-hydroxy-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以90%的产率得到2,3-dihydro-3-hydroxy-2-(2-carboxybenzyl)-1H-isoindol-1-one
  参考文献：
  名称：

  Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines

  摘要：

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10359-3
• 作为产物：
  描述：

  邻溴苯甲酸甲酯 在 盐酸 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2,3-dihydro-3-hydroxy-2-(2-methoxycarbonylbenzyl)-1H-isoindol-1-one
  参考文献：
  名称：

  Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines

  摘要：

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10359-3

文献信息

• Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols
  作者：Pascal Pigeon、Aı̈cha Mamouni、Jana Sikoraiova、Stefan Marchalin、Bernard Decroix

  DOI：10.1016/s0040-4020(01)00437-9

  日期：2001.6

  Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular pi -stacking (benzene-benzene or benzene-thiophene interaction) which did not occur in 10a (succinimide series). (C) 2001 Elsevier Science Ltd. All rights reserved.
• A New Access to Isoindolo[2,1-b][2,4]benzodiazepines through an N-Acyliminium Ion - Amide Cyclization
  作者：Pascal Pigeon、Bernard Decroix

  DOI：10.1016/s0040-4039(97)00539-x

  日期：1997.4

  Isoindolo[2,1-b][2,4]benzodiazepines 11a-c were synthesized from hydroxylactam-acid 5 when it was treated successively with thionyl chloride, ammonia (or an alkylamine) and p-toluenesulfonic acid. (C) 1997 Elsevier Science Ltd.
• Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines
  作者：Pascal Pigeon、Mohamed Othman、Pierre Netchitailo、Bernard Decroix

  DOI：10.1016/s0040-4020(97)10359-3

  日期：1998.2

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.