(3S,12bS)-3-ethyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one | 1246832-74-5

• 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: (3S,12bS)-3-ethyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
• 英文别名: (3S,12bS)-3-ethyl-12-(4-methylphenyl)sulfonyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2-one
• CAS: 1246832-74-5
• 化学式: C₂₄H₂₆N₂O₃S
• 分子量: 422.548
• InChiKey: PRKQZPAPZYUUJG-JTSKRJEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,12bS)-3-ethyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 水 、 对甲苯磺酸 、 红铝 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 6.38h， 生成 (3S,6'S,8a'S)-6'-ethyl-2',3',5',6',8',8a'-hexahydro-7'H-spiro[indoline-3,1'-indolizine]-2,7'-dione
  参考文献：
  名称：

  Formal Syntheses of Dihydrocorynantheine and Isorhynchophylline via Proline Catalyzed Mannich-Michael Reaction

  摘要：

  Proline catalyzed Mannich-Michael reaction of 3-ethyl-3-buten-2-one with 9-tosyl-3,4-dihydro-beta-carboline proceeded in a highly stereoselective manner. The reaction was applied to formal syntheses of dihydrocorynantheine and isorhynchophylline.

  DOI：

  10.3987/com-09-11828
• 作为产物：
  描述：

  色胺 在 （2S）-2-[[[[[[（（1R，2R）-2-氨基环己基]氨基]硫代甲基]氨基]-N-（二苯甲基）-N，3,3-三甲基丁酰胺 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 259.0h， 生成 (3S,12bS)-3-ethyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 、 (3R,12bS)-3-ethyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
  参考文献：
  名称：

  Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas

  摘要：

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

  DOI：

  10.1021/ja310718f

文献信息

• Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas
  作者：Mathieu P. Lalonde、Meredeth A. McGowan、Naomi S. Rajapaksa、Eric N. Jacobsen

  DOI：10.1021/ja310718f

  日期：2013.2.6

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.
• Formal Syntheses of Dihydrocorynantheine and Isorhynchophylline via Proline Catalyzed Mannich-Michael Reaction
  作者：Takashi Itoh、Hitomi Ishikawa、Ayako Tanaka、Michiko Miyazaki、Takuya Kanemitsu、Kazuhiro Nagata

  DOI：10.3987/com-09-11828

  日期：——

  Proline catalyzed Mannich-Michael reaction of 3-ethyl-3-buten-2-one with 9-tosyl-3,4-dihydro-beta-carboline proceeded in a highly stereoselective manner. The reaction was applied to formal syntheses of dihydrocorynantheine and isorhynchophylline.