(1S,2R,4R,6R)-3-oxatricyclo[4.3.0.02,4]non-7-en-5-one | 1073427-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2R,4R,6R)-3-oxatricyclo[4.3.0.02,4]non-7-en-5-one
• CAS: 1073427-02-7
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: APRDXCCOGNRMJE-ROHCDXGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R,6R)-3-oxatricyclo[4.3.0.02,4]non-7-en-5-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (1S,2R,4S,5S,6R)-3-oxatricyclo[4.3.0.02,4]non-7-en-5-ol
  参考文献：
  名称：

  Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

  摘要：

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

  DOI：

  10.1021/jo1000274

文献信息

• Total Synthesis of 15-D_2t- and 15-<i>epi</i>-15-E_2t-Isoprostanes
  作者：Yasmin Brinkmann、Camille Oger、Alexandre Guy、Thierry Durand、Jean-Marie Galano

  DOI：10.1021/jo1000274

  日期：2010.4.2

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.