1,3-cyclopentadiene-1-undecanoic acid | 321743-44-6

• 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: 1,3-cyclopentadiene-1-undecanoic acid
• 英文别名: 1,3-Cyclopenta-diene-1-undecanoic acid；11-cyclopenta-1,3-dien-1-ylundecanoic acid
• CAS: 321743-44-6
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: GMIHKJRYWTWYJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-cyclopentadiene-1-undecanoic acid 在 盐酸 、 硫酸 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 endo-1,4-bis(methyl undecanoate)-tricyclo[5.2.1.0^2,6]deca-4,8-diene
  参考文献：
  名称：

  由（R）-羟基丁二酸甲酯合成二聚体和低聚物

  摘要：

  AbstractWe report synthesis and characterization of dimer and oligomer acids from chaulmoogra oil. (R)‐Methyl hydnocarpate (methyl ester of the major fatty acid component of chaulmoogra oil) was brominated to give threo‐2,3‐dibromocyclopentane‐1‐methyl undecanoate. Formation of two diastereoisomers, viz., threo‐2(R),3(R)‐dibromocyclopentane‐1(R)‐methyl undecanoate and threo‐2(S),3(S)‐dibromocyclopentane‐(R)‐1‐methyl undecanoate, was observed. Dehydrobromination of bromo derivatives using alcoholic KOH gave a cyclopentadiene derivative as intermediate, which underwent Diels‐Alder reaction to give dimer and oligomer fatty acids. The products were characterized by ultraviolet, direct exposure probe‐mass spectroscopy, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopic techniques.

  DOI：

  10.1007/s11746-000-0173-7
• 作为产物：
  描述：

  threo-2(R),3(R)-dibromo cyclopentane-1(R)-methyl undecanoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 1,3-cyclopentadiene-1-undecanoic acid
  参考文献：
  名称：

  由（R）-羟基丁二酸甲酯合成二聚体和低聚物

  摘要：

  AbstractWe report synthesis and characterization of dimer and oligomer acids from chaulmoogra oil. (R)‐Methyl hydnocarpate (methyl ester of the major fatty acid component of chaulmoogra oil) was brominated to give threo‐2,3‐dibromocyclopentane‐1‐methyl undecanoate. Formation of two diastereoisomers, viz., threo‐2(R),3(R)‐dibromocyclopentane‐1(R)‐methyl undecanoate and threo‐2(S),3(S)‐dibromocyclopentane‐(R)‐1‐methyl undecanoate, was observed. Dehydrobromination of bromo derivatives using alcoholic KOH gave a cyclopentadiene derivative as intermediate, which underwent Diels‐Alder reaction to give dimer and oligomer fatty acids. The products were characterized by ultraviolet, direct exposure probe‐mass spectroscopy, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopic techniques.

  DOI：

  10.1007/s11746-000-0173-7