methyl 2-[3-[2-(dibenzylamino)ethyl]-1-formylindol-2-yl]-3-hydroxyprop-2-enoate | 146681-83-6

• 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: methyl 2-[3-[2-(dibenzylamino)ethyl]-1-formylindol-2-yl]-3-hydroxyprop-2-enoate
• CAS: 146681-83-6
• 化学式: C₂₉H₂₈N₂O₄
• 分子量: 468.552
• InChiKey: YDORBEGITMUMCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 2-[3-[2-(dibenzylamino)ethyl]-1-formylindol-2-yl]-3-hydroxyprop-2-enoate 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 以87%的产率得到methyl 2-[3-[2-(dibenzylamino)ethyl]-1-formylindol-2-yl]-3-methoxyprop-2-enoate
  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 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 14.5h， 生成 methyl 2-[3-[2-(dibenzylamino)ethyl]-1-formylindol-2-yl]-3-hydroxyprop-2-enoate
  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