4'-(4-chlorobenzyl)-2',3',4',5',6',7'-hexahydrospiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',6',7'-trione | 321918-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂螺环衍生物
• 英文名称: 4'-(4-chlorobenzyl)-2',3',4',5',6',7'-hexahydrospiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',6',7'-trione
• 英文别名: 4-[(4-Chlorophenyl)methyl]-4,7-diazaspiro[2.6]nonane-5,8,9-trione
• CAS: 321918-25-6
• 化学式: C₁₄H₁₃ClN₂O₃
• 分子量: 292.722
• InChiKey: XSPIFIVECHTJFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4'-(4-chlorobenzyl)-2',3',4',5',6',7'-hexahydrospiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',6',7'-trione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 96.5h， 生成 1-(4-chlorobenzyl)-2,3,4,5-tetrahydrofuro[1H][3,2-e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  Facile Preparation of Hexahydropyrrolo[3,2-e][1,4]diazepine- 2,5-diones and Tetrahydrofuro[1H][3,2-e][1,4]diazepine- 2,5-diones by Rearrangements of Cyclopropylketimines and Cyclopropylketones

  摘要：

  [GRAPHICS]Chlorolactames 2a-f reacted with sodium azide to give the cyclopropylketimines 3a-f (75-89%), and acid hydrolysis of 3c,d yielded the cyclopropylketones 6c,d (61-67%), Compounds 3a-f and 6c,d were transformed by heating (170-240 degreesC, sublimation) to the air-sensitive dihydropyrroles 4a-f (51-71%) and dihydrofurans 7c,d (85-91%), Oxidation of the dihydro derivatives 4a-f and 7c,d with DDQ led to novel types of pyrrolo[3,2-e][1,4]diazepinedione derivatives 5a-f (75-84%) and furo[H-1][3,2-e][1,4]diazepinediones 8c,d (91-93%).

  DOI：

  10.1021/ol0068187
• 作为产物：
  描述：

  4'-(4-chlorobenzyl)-2',3',4',5',6',7'-hexahydro-6'-iminospiro(cyclopropane-1,5'-[1H][1,4]-diazepine)-3',7'-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以61%的产率得到4'-(4-chlorobenzyl)-2',3',4',5',6',7'-hexahydrospiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',6',7'-trione
  参考文献：
  名称：

  Facile Preparation of Hexahydropyrrolo[3,2-e][1,4]diazepine- 2,5-diones and Tetrahydrofuro[1H][3,2-e][1,4]diazepine- 2,5-diones by Rearrangements of Cyclopropylketimines and Cyclopropylketones

  摘要：

  [GRAPHICS]Chlorolactames 2a-f reacted with sodium azide to give the cyclopropylketimines 3a-f (75-89%), and acid hydrolysis of 3c,d yielded the cyclopropylketones 6c,d (61-67%), Compounds 3a-f and 6c,d were transformed by heating (170-240 degreesC, sublimation) to the air-sensitive dihydropyrroles 4a-f (51-71%) and dihydrofurans 7c,d (85-91%), Oxidation of the dihydro derivatives 4a-f and 7c,d with DDQ led to novel types of pyrrolo[3,2-e][1,4]diazepinedione derivatives 5a-f (75-84%) and furo[H-1][3,2-e][1,4]diazepinediones 8c,d (91-93%).

  DOI：

  10.1021/ol0068187