N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine | 146681-79-0

• 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: N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine
• 英文别名: [3-[2-(dibenzylamino)ethyl]-1H-indol-2-yl]methyl benzoate
• CAS: 146681-79-0
• 化学式: C₃₂H₃₀N₂O₂
• 分子量: 474.602
• InChiKey: DNTFVVVGYGJLCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine 在 盐酸 、 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 6.5h， 生成 2-[3-[2-(dibenzylamino)ethyl]-1H-indol-2-yl]propane-1,3-diol
  参考文献：
  名称：

  Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine

  摘要：

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

  DOI：

  10.1021/jo00058a025
• 作为产物：
  描述：

  N_b,N_b-dibenzyl-2-(ethoxycarbonyl)tryptamine 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine
  参考文献：
  名称：

  Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine

  摘要：

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

  DOI：

  10.1021/jo00058a025

文献信息

• Synthesis of vinca alkaloids and related compounds. 63. A new synthetic pathway for preparing alkaloids and related compounds with the aspidosperma skeleton. Total syntheses of (.+-.)-vincadifformine, (.+-.)-tabersonine, and (.+-.)-oxotabersonine
  作者：Gyorgy Kalaus、Istvan Greiner、Maria Kajtar-Peredy、Janos Brlik、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00058a025

  日期：1993.3

  Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.