(R)-11,12b-dimethyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one | 1178541-63-3

• 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)-11,12b-dimethyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one
• 英文别名: (12bR)-11,12b-dimethyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one；(12bR)-11,12b-dimethyl-1,2,3,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one
• CAS: 1178541-63-3
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: MTSJRGFMLSXZAM-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  7-甲基色胺 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 、 4-二甲氨基吡啶 、 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.08h， 生成 (R)-11,12b-dimethyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h

文献信息

• Enantioselective Brønsted Acid-Catalyzed <i>N</i>-Acyliminium Cyclization Cascades
  作者：Michael E. Muratore、Chloe A. Holloway、Adam W. Pilling、R. Ian Storer、Graham Trevitt、Darren J. Dixon

  DOI：10.1021/ja9024885

  日期：2009.8.12

  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.
• Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/<i>N</i>-Sulfonyliminium Cyclization Cascade
  作者：Alex W. Gregory、Pavol Jakubec、Paul Turner、Darren J. Dixon

  DOI：10.1021/ol401784h

  日期：2013.9.6

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.