lauryl albifloranine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 依波格型生物碱
• 英文名称: lauryl albifloranine
• 英文别名: methyl (1S,15R,17R,18S)-17-(2-dodecanoyloxyethyl)-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
• 化学式: C₃₃H₄₈N₂O₄
• 分子量: 536.755
• InChiKey: MBKWLRGTSSAVAT-USAQXFLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl 3-benzyl-1,2,3,4,5,7,8-octahydro-5-[2-ξ-(1,3-dioxolan-2-yl)-4-benzyloxy-1-butyl]azonino[5,4-b]indole-carboxylate 在 4-二甲氨基吡啶 、 palladium on activated charcoal 盐酸 、 氢气 、 ammonium formate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~130.0 ℃ 、101.33 kPa 条件下， 反应 59.0h， 生成 lauryl albifloranine
  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