3-Ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-4-carbonitrile | 124321-60-4

• 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: 3-Ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-4-carbonitrile
• CAS: 124321-60-4
• 化学式: C₁₈H₁₉N₃
• 分子量: 277.369
• InChiKey: OYOPQYNBOKOYOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-4-carbonitrile 在 platinum(IV) oxide silver tetrafluoroborate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 dimethyl 2-[(2R,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]propanedioate
  参考文献：
  名称：

  Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine

  摘要：

  Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of 3-ethylindolo[2,3-a]quinolizidine 4a (regenerated from the corresponding alpha-aminonitrile 4b) afforded enamine 5. Catalytic hydrogenation of compound 5, led stereoselectively to compound 6 (pseudo), which is the highly desired intermediate for the preparation of several Corynanthe alkaloids, including (+/-)-hirsutine 7. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00056-7
• 作为产物：
  描述：

  5-Ethyl-1-<2-(3-indolyl)ethyl>-1,2,3,6-tetrahydropyridine-2-carbonitrile 在 sodium acetate 、 溶剂黄146 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 反应 76.0h， 生成 3-Ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-4-carbonitrile
  参考文献：
  名称：

  Indoloquinolizidine iminium species formed under the modified Polonovski reaction conditions

  摘要：

  DOI：

  10.1016/s0040-4020(01)80098-3

文献信息

• TAMMINEN, TARJA;JOKELA, REIJA;TIRKKONEN, BIRGIT;LOUNASMAA, MAURI, TETRAHEDRON, 45,(1989) N, C. 2683-2692
  作者：TAMMINEN, TARJA、JOKELA, REIJA、TIRKKONEN, BIRGIT、LOUNASMAA, MAURI

  DOI：——

  日期：——
• Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine
  作者：Mauri Lounasmaa、Jari Miettinen、Pirjo Hanhinen、Reija Jokela

  DOI：10.1016/s0040-4039(97)00056-7

  日期：1997.2

  Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of 3-ethylindolo[2,3-a]quinolizidine 4a (regenerated from the corresponding alpha-aminonitrile 4b) afforded enamine 5. Catalytic hydrogenation of compound 5, led stereoselectively to compound 6 (pseudo), which is the highly desired intermediate for the preparation of several Corynanthe alkaloids, including (+/-)-hirsutine 7. (C) 1997 Elsevier Science Ltd.
• Indoloquinolizidine iminium species formed under the modified Polonovski reaction conditions
  作者：Tarja Tamminen、Reija Jokela、Birgit Tirkkonen、Mauri Lounasmaa

  DOI：10.1016/s0040-4020(01)80098-3

  日期：1989.1