11-benzyl-11b-methyl-2,3,5,6,11,11b-hexahydroindolizino[8,7-b]indol-1-one | 874916-40-2

• 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: 11-benzyl-11b-methyl-2,3,5,6,11,11b-hexahydroindolizino[8,7-b]indol-1-one
• 英文别名: 11-Benzyl-11b-methyl-2,3,5,6-tetrahydroindolizino[8,7-b]indol-1-one
• CAS: 874916-40-2
• 化学式: C₂₂H₂₂N₂O
• 分子量: 330.429
• InChiKey: DURYGSGGKUSMCH-UHFFFAOYSA-N

物化性质

• 沸点：
  530.0±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-benzyl-11b-methyl-2,3,5,6,11,11b-hexahydroindolizino[8,7-b]indol-1-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 11-benzyl-1-(1-hydroxymethylpropyl)-11b-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indol-1-ol
  参考文献：
  名称：

  Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B

  摘要：

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.

  DOI：

  10.1021/ol0526367
• 作为产物：
  描述：

  2-(1-苄基-1H-吲哚-3-基)-乙胺 在 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 48.0h， 生成 11-benzyl-11b-methyl-2,3,5,6,11,11b-hexahydroindolizino[8,7-b]indol-1-one
  参考文献：
  名称：

  Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B

  摘要：

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.

  DOI：

  10.1021/ol0526367

文献信息

• Facile Construction of the Pentacyclic Framework of Subincanadine B. Synthesis of 20-Deethylenylated Subincanadine B and 19,20-Dihydrosubincanadine B
  作者：Yanqin Liu、Shengjun Luo、Xingnian Fu、Fang、Zeyang Zhuang、Wanting Xiong、Xueshun Jia、Hongbin Zhai

  DOI：10.1021/ol0526367

  日期：2006.1.1

  We describe a facile approach for effectively constructing the pentacyclic framework of subincanadine B. The seven-step assembly of tetracyclic ketone 14 featured Michael addition, Pictet-Spengler cyclization, and Dieckmann condensation. From this key ketone intermediate, two analogues of subincanadine 13, i.e., 20-deethylenylated subincanadine B (27) and 19,20-dihydrosubincanadine B (31), were synthesized in four steps, respectively.