(3S,6R,7aR)-3-tert-Butyl-6-ethyl-6-(4-hydroxy-butyl)-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one | 139125-51-2

• 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: (3S,6R,7aR)-3-tert-Butyl-6-ethyl-6-(4-hydroxy-butyl)-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• 英文别名: (3S,6R,7aR)-3-tert-butyl-6-ethyl-6-(4-hydroxybutyl)-7a-methyl-3,7-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 139125-51-2
• 化学式: C₁₇H₃₁NO₃
• 分子量: 297.438
• InChiKey: QYYOKOBNWUIOBD-KBRIMQKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 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,7aR)-3-tert-Butyl-6-ethyl-6-(4-hydroxy-butyl)-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到(3S,6R,7aR)-6-(4-Bromo-butyl)-3-tert-butyl-6-ethyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-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
• 作为产物：
  描述：

  (3S,6R,7aR)-6-But-3-enyl-3-tert-butyl-6-ethyl-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 生成 (3S,6R,7aR)-3-tert-Butyl-6-ethyl-6-(4-hydroxy-butyl)-7a-methyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-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.