4-((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester | 677309-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester
• CAS: 677309-12-5
• 化学式: C₁₈H₃₀O₅Si
• 分子量: 354.519
• InChiKey: VESANJGMNXYKMU-NGEKVNGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-3-oxo-butyric acid ethyl ester 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 以77%的产率得到2-Diazo-4-((1S,2R,3S,4S,5R)-2,4-dimethyl-3-trimethylsilanyloxy-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
• 作为产物：
  描述：

  (1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 在 2,6-二甲基吡啶 、 正丁基锂 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 4-((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-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