(S)-8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one | 705927-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one
• 英文别名: (8aS)-8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one
• CAS: 705927-08-8
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: IRPQISJRGTUBDC-QMMMGPOBSA-N

物化性质

• 沸点：
  268.4±20.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one 在 N-甲基吗啉 、 吡啶 、 四氧化锇 、 lithium aluminium tetrahydride 、 三氯化铝 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 81.0h， 生成 (8R,8aS)-8-Hydroxy-8-methyl-7(1H)-octahydroindolizinone
  参考文献：
  名称：

  Rapid Stereoselective Access to Key Pumiliotoxin Precursors from a Common Intermediate

  摘要：

  Epoxidation and dihydroxylation of 8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one proceeded from the concave face with good selectivity and gave advanced precursors for pumiliotoxin and allopumiliotoxin synthesis, respectively. The origin of the selectivity is believed to be stereoelectronic in nature and allows rapid entry to three different pumiliotoxin classes from a common intermediate.

  DOI：

  10.1021/jo0497205
• 作为产物：
  描述：

  (S)-2-isopropenylpyrrolidine-1-carboxylic acid tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 氰基磷酸二乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 (S)-8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one
  参考文献：
  名称：

  Rapid Stereoselective Access to Key Pumiliotoxin Precursors from a Common Intermediate

  摘要：

  Epoxidation and dihydroxylation of 8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one proceeded from the concave face with good selectivity and gave advanced precursors for pumiliotoxin and allopumiliotoxin synthesis, respectively. The origin of the selectivity is believed to be stereoelectronic in nature and allows rapid entry to three different pumiliotoxin classes from a common intermediate.

  DOI：

  10.1021/jo0497205

文献信息

• Stereoselective synthesis of (8R,8aS)-8-methylhexahydroindolizin-5-one
  作者：Paul Armstrong、Gavin O’Mahony、Paul J. Stevenson、Andrew D. Walker

  DOI：10.1016/j.tetlet.2005.09.133

  日期：2005.11

  Catalytic hydrogenation of dihydroindolizidinone occurred preferentially from the endo-face giving rapid entry to (8R,8aS)-8-methylhexahydroindolizin-5-one, a key intermediate in the synthesis of 5,8-disubstituted indolizidines and deoxypumiliotoxin 25 1 H. The selectivity could be improved further by diimide reduction though this also resulted in some oxidation of the alkene to the diene. The basis of the unusual stereoselectivity in the diimide reduction is believed to be stereoelectronic in origin. (c) 2005 Elsevier Ltd. All rights reserved.
• Rapid Stereoselective Access to Key Pumiliotoxin Precursors from a Common Intermediate
  作者：Gavin O'Mahony、Mark Nieuwenhuyzen、Paul Armstrong、Paul J. Stevenson

  DOI：10.1021/jo0497205

  日期：2004.5.1

  Epoxidation and dihydroxylation of 8-methyl-2,3,6,8a-tetrahydro-1H-indolizin-5-one proceeded from the concave face with good selectivity and gave advanced precursors for pumiliotoxin and allopumiliotoxin synthesis, respectively. The origin of the selectivity is believed to be stereoelectronic in nature and allows rapid entry to three different pumiliotoxin classes from a common intermediate.