9-benzyl-2-(2-methoxycarbonylethyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester | 874916-39-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 9-benzyl-2-(2-methoxycarbonylethyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester
• 英文别名: Methyl 9-benzyl-2-(3-methoxy-3-oxopropyl)-1-methyl-3,4-dihydropyrido[3,4-b]indole-1-carboxylate
• CAS: 874916-39-9
• 化学式: C₂₅H₂₈N₂O₄
• 分子量: 420.508
• InChiKey: NTCSZSHZIREVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-(2-methoxycarbonylethyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (11-benzyl-1-hydroxy-11b-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indol-1-yl)acetic acid ethyl ester
  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 三氟乙酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 43.0h， 生成 9-benzyl-2-(2-methoxycarbonylethyl)-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid methyl ester
  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