methyl 7-methylene-6-oxo-1,3,4,5,6,7-hexahydro-azocino[4,5,6-cd]indole-4-carboxylate | 871575-32-5

• 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: methyl 7-methylene-6-oxo-1,3,4,5,6,7-hexahydro-azocino[4,5,6-cd]indole-4-carboxylate
• 英文别名: methyl (12S)-9-methylidene-10-oxo-3,11-diazatricyclo[6.5.1.04,14]tetradeca-1,4,6,8(14)-tetraene-12-carboxylate
• CAS: 871575-32-5
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: PLQULGQTFCYQSR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 7-methylene-6-oxo-1,3,4,5,6,7-hexahydro-azocino[4,5,6-cd]indole-4-carboxylate 在 palladium on activated charcoal titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 氨 、 氢气 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 91.0h， 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 以 乙腈 为溶剂， 反应 3.0h， 以53%的产率得到methyl 7-methylene-6-oxo-1,3,4,5,6,7-hexahydro-azocino[4,5,6-cd]indole-4-carboxylate
  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

文献信息

• Dragmacidin E Synthesis Studies. Preparation of a Model Cycloheptannelated Indole Fragment
  作者：Ken S. Feldman、Paiboon Ngernmeesri

  DOI：10.1021/ol0522081

  日期：2005.11.1

  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.