(R)-8-bromo-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one | 1178541-68-8

• 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: (R)-8-bromo-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
• 英文别名: (11bR)-8-bromo-11b-dodecyl-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 1178541-68-8
• 化学式: C₂₆H₃₇BrN₂O
• 分子量: 473.497
• InChiKey: PNYXGZUYWSAFGQ-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(5-溴-1H-吲哚-3-基)乙胺 、 hexadec-3-ynoic acid 在 [Au(Cl)PPh₃] 、 silver trifluoromethanesulfonate 、 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 作用下， 以 甲苯 为溶剂， 反应 49.0h， 生成 (S)-8-bromo-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one 、 (R)-8-bromo-11b-dodecyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885