4-((1S,2R,3S,4S,5R)-3-Hydroxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester | 677309-11-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-((1S,2R,3S,4S,5R)-3-Hydroxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester
• CAS: 677309-11-4
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: CTYFXYRRLVQBNE-HBYZYFPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((1S,2R,3S,4S,5R)-3-Hydroxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester 在 2,6-二甲基吡啶 、 dirhodium tetraacetate 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 sodium chloride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 生成 (1R,2R,6R,7R,8S)-2,7-dimethyl-6-trimethylsilyloxy-11-oxatricyclo[6.2.1.02,6]undec-9-en-4-one
  参考文献：
  名称：

  Desymmetrizations of meso oxabicyclic compounds by asymmetric C–H insertion

  摘要：

  meso Oxabicyclo[3.2.1]diazoketones underwent intramolecular C-H bond insertion to generate oxatricyclic compounds bearing fused cyclopentanones upon reaction with rhodium catalysts. Using the chiral catalyst Rh-2(S-BPTTL)(4), 44% ee was achieved in this desymmetrization reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.055
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 (1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 在 正丁基锂 、 sodium hydride 作用下， 以95%的产率得到4-((1S,2R,3S,4S,5R)-3-Hydroxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  Desymmetrizations of meso oxabicyclic compounds by asymmetric C–H insertion

  摘要：

  meso Oxabicyclo[3.2.1]diazoketones underwent intramolecular C-H bond insertion to generate oxatricyclic compounds bearing fused cyclopentanones upon reaction with rhodium catalysts. Using the chiral catalyst Rh-2(S-BPTTL)(4), 44% ee was achieved in this desymmetrization reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.055