(3S,6R,8S,9R)-1-aza-3-(3-butenyl)-9-hydroxymethyl-3,6-dimethyl-8-phenyl-7-oxabicyclo[4.3.0]nonan-2-one | 153683-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3S,6R,8S,9R)-1-aza-3-(3-butenyl)-9-hydroxymethyl-3,6-dimethyl-8-phenyl-7-oxabicyclo[4.3.0]nonan-2-one
• 英文别名: (2S,3S,6R,8aR)-6-but-3-enyl-3-(hydroxymethyl)-6,8a-dimethyl-2-phenyl-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 153683-06-8
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: SYAYFEHTKKECKJ-RAUXBKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,6R,8S,9R)-1-aza-3-(3-butenyl)-9-hydroxymethyl-3,6-dimethyl-8-phenyl-7-oxabicyclo[4.3.0]nonan-2-one 在 红铝 、 四丁基磷酸氢铵 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 36.0h， 以65%的产率得到(R)-4-(3-butenyl)-4-methyl-2-cyclohexenone
  参考文献：
  名称：

  (-)-Dehydrochamaecynenol 的正式合成。高级密钥中间体的非对称合成

  摘要：

  Keto ester (2), which served as an advanced intermediate in the total synthesis of (+/-)-dehydrochamaecynenol (1), has been prepared in optically active form.

  DOI：

  10.3987/com-99-s139
• 作为产物：
  描述：

  (2S,3S,8aR)-Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-5-oxo-5H-oxazolo<3,2-a>pyridine 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.67h， 生成 (3S,6R,8S,9R)-1-aza-3-(3-butenyl)-9-hydroxymethyl-3,6-dimethyl-8-phenyl-7-oxabicyclo[4.3.0]nonan-2-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams

  摘要：

  A route to the titled compounds in >99 % ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated from marine organisms, was prepared in high enantiomeric excess.

  DOI：

  10.1021/jo00078a032

文献信息

• Synthesis of enantiomerically pure hydrinden-2-ones and benz[e]inden-2-ones via asymmetric alkylations of chiral bicyclic lactams
  作者：Lawrence Snyder、A. I. Meyers

  DOI：10.1021/jo00078a032

  日期：1993.12

  A route to the titled compounds in >99 % ee was achieved from sequential diastereoselective alkylations of chiral, nonracemic bicyclic lactams 6 and 15. An intramolecular addition of the organolithium species derived from 17a-c and 28a-d gave, after hydrolysis, diketones 25a-c and 30a-d, which were cyclized to the titled compounds 4a-c and 31a-d. As an example of the versatility of this method, the ABC ring system of the triterpene stelliferin A, isolated from marine organisms, was prepared in high enantiomeric excess.
• A Formal Synthesis of (-)-Dehydrochamaecynenol. Asymmetric Synthesis of an Advanced Key Intermediate
  作者：Hsing-Jang Liu、Daqing Sun

  DOI：10.3987/com-99-s139

  日期：——

  Keto ester (2), which served as an advanced intermediate in the total synthesis of (+/-)-dehydrochamaecynenol (1), has been prepared in optically active form.