7-Benzyl-9-(2-[1,3]dioxolan-2-yl-4-methoxy-butyl)-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid methyl ester | 247088-77-3

• 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: 7-Benzyl-9-(2-[1,3]dioxolan-2-yl-4-methoxy-butyl)-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid methyl ester
• 英文别名: methyl 3-benzyl-5-[2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,4,5,6,7,8-hexahydro-1H-azonino[5,4-b]indole-7-carboxylate
• CAS: 247088-77-3
• 化学式: C₃₁H₄₀N₂O₅
• 分子量: 520.669
• InChiKey: ZMXGOPBUYBGCLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-Benzyl-9-(2-[1,3]dioxolan-2-yl-4-methoxy-butyl)-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成
  参考文献：
  名称：

  Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine

  摘要：

  Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) with 4-(1,3-dioxolan-2-yl)-6-benzylaxyhexanal (11a) provided the tetracyclic intermediates methyl (3aSR,4RS,11bRS)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-zeta-(1,3-dioxalan-2-yl)-4-benzyloxy)-1-butyl]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates (14a,15a), which were further elaborated to afford racemic albifloranine (3). The first total synthesis of albifloranine was completed in 13 steps, with an overall 7% yield. Ester and ether derivatives of albifloranine were synthesized for evaluation as anti-addictive agents. Among these, 18-methoxycoronaridine (20b) stands out as a nontoxic agent that significantly reduces demand for morphine, cocaine, nicotine and alcohol in rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00513-x
• 作为产物：
  描述：

  methyl (3aSR,4RS,11bSR)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2-ξ-(1,3-dioxolan-2-yl)-4-methoxy)-1-butyl]-1H-pyrrolo[2,3-d]carbazole-6-carboxylate 在 sodium tetrahydroborate 作用下， 以 溶剂黄146 为溶剂， 以91%的产率得到7-Benzyl-9-(2-[1,3]dioxolan-2-yl-4-methoxy-butyl)-5,6,7,8,9,10,11,12-octahydro-7,12-diaza-cyclonona[a]indene-11-carboxylic acid methyl ester
  参考文献：
  名称：

  Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine

  摘要：

  Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) with 4-(1,3-dioxolan-2-yl)-6-benzylaxyhexanal (11a) provided the tetracyclic intermediates methyl (3aSR,4RS,11bRS)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-zeta-(1,3-dioxalan-2-yl)-4-benzyloxy)-1-butyl]-1H-pyrrolo[2,3-d]carbazole-6-carboxylates (14a,15a), which were further elaborated to afford racemic albifloranine (3). The first total synthesis of albifloranine was completed in 13 steps, with an overall 7% yield. Ester and ether derivatives of albifloranine were synthesized for evaluation as anti-addictive agents. Among these, 18-methoxycoronaridine (20b) stands out as a nontoxic agent that significantly reduces demand for morphine, cocaine, nicotine and alcohol in rats. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00513-x