methyl 8-<(2-methoxyethoxy)methyl>-2-methyl-7-oxo-2,5,6,7-tetrahydro-1,5-methano-1H-azonino<4,3-b>indole-4(E)-acrylate | 143466-36-8

• 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 8-<(2-methoxyethoxy)methyl>-2-methyl-7-oxo-2,5,6,7-tetrahydro-1,5-methano-1H-azonino<4,3-b>indole-4(E)-acrylate
• CAS: 143466-36-8
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: MQFCCJAEYXIROB-UMURBWECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.0
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 8-<(2-methoxyethoxy)methyl>-2-methyl-7-oxo-2,5,6,7-tetrahydro-1,5-methano-1H-azonino<4,3-b>indole-4(E)-acrylate 在 盐酸 、 sodium tetrahydroborate 作用下， 生成 rac-(1R,5S,E)-4-ethylidene-2-methyl-1,2,3,4,5,6,7,8-octahydro-1,5-methanoazonino[4,3-b]indol-7-ol
  参考文献：
  名称：

  ervitsine骨架的直接入口。16-脱亚甲基维他命的合成

  摘要：

  据报道，基于2-乙酰基吲哚烯酸酯向N-烷基-β-酰基吡啶鎓盐的亲核加成以及所得1,4-二氢吡啶中间体的进一步酸环化，合成16-脱亚甲基维他命（6）的短途径。

  DOI：

  10.1016/s0040-4039(00)74813-1
• 作为产物：
  描述：

  lithium indole-2-carboxylate 在 盐酸 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 22.0h， 生成 methyl 8-<(2-methoxyethoxy)methyl>-2-methyl-7-oxo-2,5,6,7-tetrahydro-1,5-methano-1H-azonino<4,3-b>indole-4(E)-acrylate
  参考文献：
  名称：

  Biomimetic Total Synthesis of Ervitsine and Indole Alkaloids of the Ervatamine Group via 1,4-Dihydropyridines

  摘要：

  Addition of the enolate derived from 2-acetylindole In to pyridinium salt 2 followed by in situ trapping of the initially formed 1,4-dihydropyridine 3a with Eschenmoser's salt gives tetracycle 5a. Subsequent elaboration of the exocyclic methylene and E-ethylidene substituents leads to N-a-methylervitsine (17a). A similar sequence from the N-a-protected 2-acetylindole Ic establishes the first total synthesis of the 2-acylindole alkaloid ervitsine. Alternatively, dihydropyridine 3a is trapped with BrSePh to give the tetracyclic selenide 7a, which is then converted to N-a-methylervitsine by way of selenoxide 20. The synthesis of the alkaloids of the ervatamine group starts with the addition of the enolate derived from 2-acetyl-1-benzylindole (Ig) to pyridinium salt 24 and the conversion of the resulting 1,4-dihydropyridine to 3,5-diacylated dihydropyridine 26g. Chemoselective reduction of the vinylogous amide moiety of 26g, followed by deprotection of the indole ring and LiEt3BH reduction leads to diol 37b. On sequential treatment with Eschenmoser's salt, methyl iodide, NaCNBH3, and MnO2, 37b is converted to the tetracyclic 2-acylindole 39, from which the first total synthesis of 19,20-didehydroervatamine and 20-epiervatamine is accomplished by manipulation of the l-hydroxyethyl chain. The above syntheses can be considered as biomimetic, as cyclization of the key intermediates I and II mimics the key steps of the biosynthesis of the title alkaloids.

  DOI：

  10.1021/jo9623301