(8S,8aS)-8-羟基-8-甲基-2,3,8,8a-四氢-5(1H)-吲哚嗪酮 | 705927-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (8S,8aS)-8-羟基-8-甲基-2,3,8,8a-四氢-5(1H)-吲哚嗪酮
• 英文名称: (8S,8aS)-8-hydroxy-8-methyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one
• 英文别名: (8S,8aS)-8-hydroxy-8-methyl-1,2,3,8a-tetrahydroindolizin-5-one
• CAS: 705927-10-2
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: VOASLGSTKWGRGO-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8S,8aS)-8-羟基-8-甲基-2,3,8,8a-四氢-5(1H)-吲哚嗪酮 在 palladium on activated charcoal 氢气 作用下， 20.0 ℃ 、101.32 kPa 条件下， 反应 18.0h， 以100%的产率得到(8S,8aS)-8-hydroxy-8-methylhexahydroindolizin-5(1H)-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
• 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 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成 (8S,8aS)-8-羟基-8-甲基-2,3,8,8a-四氢-5(1H)-吲哚嗪酮
  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

• 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.