tert-butyl (9R,12S)-9-methyl-10,15-dioxo-3,11-diazatetracyclo[6.5.1.19,12.04,14]pentadeca-1,4,6,8(14)-tetraene-3-carboxylate | 871575-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl (9R,12S)-9-methyl-10,15-dioxo-3,11-diazatetracyclo[6.5.1.19,12.04,14]pentadeca-1,4,6,8(14)-tetraene-3-carboxylate
• CAS: 871575-33-6
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: HZTPRYHUIAYWIR-HXPMCKFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (9R,12S)-9-methyl-10,15-dioxo-3,11-diazatetracyclo[6.5.1.19,12.04,14]pentadeca-1,4,6,8(14)-tetraene-3-carboxylate 在 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 26.0h， 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 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 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 68.0h， 生成 tert-butyl (9R,12S)-9-methyl-10,15-dioxo-3,11-diazatetracyclo[6.5.1.19,12.04,14]pentadeca-1,4,6,8(14)-tetraene-3-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.