1,5-di-tert-butyl 4-methyl 7-methylene-6-oxo-3,4,6,7-tetrahydro-azocino[4,5,6-cd]indole-1,4,5-tricarboxylate | 871575-40-5

• 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: 1,5-di-tert-butyl 4-methyl 7-methylene-6-oxo-3,4,6,7-tetrahydro-azocino[4,5,6-cd]indole-1,4,5-tricarboxylate
• CAS: 871575-40-5
• 化学式: C₂₅H₃₀N₂O₇
• 分子量: 470.522
• InChiKey: OMSQDIXTUFMZGJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104.14
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,5-di-tert-butyl 4-methyl 7-methylene-6-oxo-3,4,6,7-tetrahydro-azocino[4,5,6-cd]indole-1,4,5-tricarboxylate 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 氨 、 三仲丁基硼氢化钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 31.0h， 生成 di-tert-butyl (6R,9S,11S)-11-cyano-11-((methoxycarbonyl)amino)-6-methyl-7-oxo-6,7,9,10-tetrahydro-6,9-methanoazocino[4,5,6-cd]indole-2,8-dicarboxylate
  参考文献：
  名称：

  Dragmacidin E Synthesis Studies. Preparation of a Model Cycloheptannelated Indole Fragment

  摘要：

  The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

  DOI：

  10.1021/ol0522081
• 作为产物：
  描述：

  methyl 2-(2,2-dichloropropionylamino)-3-(1H-indol-3-yl)propionate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 1,5-di-tert-butyl 4-methyl 7-methylene-6-oxo-3,4,6,7-tetrahydro-azocino[4,5,6-cd]indole-1,4,5-tricarboxylate
  参考文献：
  名称：

  Dragmacidin E Synthesis Studies. Preparation of a Model Cycloheptannelated Indole Fragment

  摘要：

  The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

  DOI：

  10.1021/ol0522081