di-tert-butyl (6R,9S,11S)-11-amino-11-cyano-6-methyl-7-oxo-6,7,9,10-tetrahydro-6,9-methanoazocino[4,5,6-cd]indole-2,8-dicarboxylate | 871575-34-7

• 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: di-tert-butyl (6R,9S,11S)-11-amino-11-cyano-6-methyl-7-oxo-6,7,9,10-tetrahydro-6,9-methanoazocino[4,5,6-cd]indole-2,8-dicarboxylate
• CAS: 871575-34-7
• 化学式: C₂₅H₃₀N₄O₅
• 分子量: 466.537
• InChiKey: HPYAROYJPSADRP-WGXRPPGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  34.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  127.65
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (6R,9S,11S)-11-amino-11-cyano-6-methyl-7-oxo-6,7,9,10-tetrahydro-6,9-methanoazocino[4,5,6-cd]indole-2,8-dicarboxylate 在 platinum(IV) oxide 盐酸 、 lithium hydroxide 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 20.0 ℃ 、10.34 MPa 条件下， 反应 54.0h， 生成 ditert-butyl (9R,12S,15R)-9-methyl-2',10-dioxospiro[3,11-diazatetracyclo[6.5.1.19,12.04,14]pentadeca-1,4,6,8(14)-tetraene-15,4'-imidazolidine]-3,11-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：

  1,5-di-tert-butyl 4-methyl trans-7-methyl-6-oxo-3,4,6,7-tetrahydro-azocino[4,5,6-cd]indole-1,4,5-tricarboxylate 在 titanium(IV) isopropylate 、 氨 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 di-tert-butyl (6R,9S,11S)-11-amino-11-cyano-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