methyl 10-acetoxy-7-hydroxy-3,5-dioxodecanoate | 146396-32-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 10-acetoxy-7-hydroxy-3,5-dioxodecanoate
• 英文别名: Methyl 10-acetyloxy-7-hydroxy-3,5-dioxodecanoate
• CAS: 146396-32-9
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: ZNHWTBWCLCWUKX-UHFFFAOYSA-N

物化性质

• 沸点：
  451.1±45.0 °C(predicted)
• 密度：
  1.190±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 10-acetoxy-7-hydroxy-3,5-dioxodecanoate 在 titanium(IV) isopropylate 、 甲醇 、 sodium tetrahydroborate 作用下， 生成 (3R,5R,7R)-10-Acetoxy-3,5,7-trihydroxy-decanoic acid methyl ester
  参考文献：
  名称：

  Iterative diastereoselective reduction of hydroxy diketoesters to all 1,3,5 syn triols: synthesis of C1-C10 fragment of Nystatin A1

  摘要：

  the iterative diastereoselective reduction of a model hydroxy 3,5 diketo ester to the corresponding skipped 1,3,5 triol ester was studied in different conditions. The use of NaBH4/Ti(OiPr)4 in THF leads with good stereoselection to the syn-syn triol ester as the main product; the described method has been applied to an extremely short synthesis of the C1-C10 fragment (in racemic form) of the macrolide antibiotic Nystatin A1.

  DOI：

  10.1016/s0040-4020(01)81196-0
• 作为产物：
  描述：

  4-acetoxy-1-butanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 10-acetoxy-7-hydroxy-3,5-dioxodecanoate
  参考文献：
  名称：

  Iterative diastereoselective reduction of hydroxy diketoesters to all 1,3,5 syn triols: synthesis of C1-C10 fragment of Nystatin A1

  摘要：

  the iterative diastereoselective reduction of a model hydroxy 3,5 diketo ester to the corresponding skipped 1,3,5 triol ester was studied in different conditions. The use of NaBH4/Ti(OiPr)4 in THF leads with good stereoselection to the syn-syn triol ester as the main product; the described method has been applied to an extremely short synthesis of the C1-C10 fragment (in racemic form) of the macrolide antibiotic Nystatin A1.

  DOI：

  10.1016/s0040-4020(01)81196-0