2',3',4',5',6',7'-hexahydro-6'-imino-4'-pentylspiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',7'-dione | 321918-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',3',4',5',6',7'-hexahydro-6'-imino-4'-pentylspiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',7'-dione
• 英文别名: 9-Imino-4-pentyl-4,7-diazaspiro[2.6]nonane-5,8-dione
• CAS: 321918-06-3
• 化学式: C₁₂H₁₉N₃O₂
• 分子量: 237.302
• InChiKey: PTHMOUYEKVXXPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  73.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2',3',4',5',6',7'-hexahydro-6'-imino-4'-pentylspiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',7'-dione 180.0~240.0 ℃ 、0.01 Pa 条件下， 反应 0.5h， 生成 1-Pentyl-1,3,4,6,7,8-hexahydro-pyrrolo[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：

  6'-chlorohexahydro-4'-pentylspiro(cyclopropane-1,5'-<1H><1,4>diazepine)-3',7'-dione 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以89%的产率得到2',3',4',5',6',7'-hexahydro-6'-imino-4'-pentylspiro(cyclopropane-1,5'-[1H][1,4]diazepine)-3',7'-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

文献信息

• Facile Preparation of Hexahydropyrrolo[3,2-<i>e</i>][1,4]diazepine- 2,5-diones and Tetrahydrofuro[1<i>H</i>][3,2-<i>e</i>][1,4]diazepine- 2,5-diones by Rearrangements of Cyclopropylketimines and Cyclopropylketones
  作者：Christian Funke、Mazen Es-Sayed、Armin de Meijere

  DOI：10.1021/ol0068187

  日期：2000.12.1

  [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%).