((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-acetic acid | 677309-18-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-acetic acid
• CAS: 677309-18-1
• 化学式: C₁₄H₂₄O₄Si
• 分子量: 284.428
• InChiKey: SKOZTMWDIYFMFW-VWZYITTGSA-N

物化性质

• 沸点：
  355.0±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-acetic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-3-yl)-acetic acid
  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 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 生成 ((1R,2S,3S,4R,5S)-2,4-Dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-3-yl)-acetic acid
  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