1-(4-chlorophenyl)-6,7-dihydrospiro[indole-3,1'-isoindoline]-2,3',4(1H,5H)-trione | 1579950-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(4-chlorophenyl)-6,7-dihydrospiro[indole-3,1'-isoindoline]-2,3',4(1H,5H)-trione
• CAS: 1579950-56-3
• 化学式: C₂₁H₁₅ClN₂O₃
• 分子量: 378.815
• InChiKey: TYMWIUAGKNNUNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-6,7-dihydrospiro[indole-3,1'-isoindoline]-2,3',4(1H,5H)-trione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 30.0h， 以89%的产率得到4-hydroxy-1-(4-chlorophenyl)spiro[indoline-3,1'-isoindoline]-2,3'-dione
  参考文献：
  名称：

  (±)-CSA catalyzed one-pot synthesis of 6,7-dihydrospiro[indole-3,1′-isoindoline]-2,3′,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids

  摘要：

  The domino dehydration/condensation/cyclization sequence reaction of cyclic enaminones with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one derivatives has been successfully realized for the first time in toluene at 90 C by using a catalytic amount of commercially available inexpensive (+/-)-CSA (30 mol %). Gratifyingly, this novel domino protocol provides good to excellent yields of previously unknown class of 1-aryl/alkyl-substituted 6,7-dihydrospiro[indole-3,1 '-isoindoline]-2,3,4(111,5H)-trione derivatives. Moreover, biologically attractive spirooxindoles and ibophyllidine-like alkaloids have been prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.154
• 作为产物：
  描述：

  3-[(4-氯苯基)氨基]-1-环己-2-烯酮 、 1-羟基-3-氧代-2H-异吲哚-1-羧酸乙酯 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以75%的产率得到1-(4-chlorophenyl)-6,7-dihydrospiro[indole-3,1'-isoindoline]-2,3',4(1H,5H)-trione
  参考文献：
  名称：

  (±)-CSA catalyzed one-pot synthesis of 6,7-dihydrospiro[indole-3,1′-isoindoline]-2,3′,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids

  摘要：

  The domino dehydration/condensation/cyclization sequence reaction of cyclic enaminones with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one derivatives has been successfully realized for the first time in toluene at 90 C by using a catalytic amount of commercially available inexpensive (+/-)-CSA (30 mol %). Gratifyingly, this novel domino protocol provides good to excellent yields of previously unknown class of 1-aryl/alkyl-substituted 6,7-dihydrospiro[indole-3,1 '-isoindoline]-2,3,4(111,5H)-trione derivatives. Moreover, biologically attractive spirooxindoles and ibophyllidine-like alkaloids have been prepared. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.154