methyl 6-oxatetradecanoate | 131178-93-3

• 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 6-oxatetradecanoate
• 英文别名: methyl 5-octoxypentanoate
• CAS: 131178-93-3
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: MGDABVATSBBDHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-碘戊酸甲酯 、 辛醇 生成 methyl 6-oxatetradecanoate
  参考文献：
  名称：

  KATOH, AKIRA;LU, TIANBAO;DEVADAS, B.;ADAMS, STEVEN P.;GORDON, JEFFREY I.;+, J. ORG. CHEM., 56,(1991) N, C. 731-735

  摘要：

  DOI：

文献信息

• Nucleophile-dependent substitution reactions of 5-halovaleric acid esters: synthesis of 6,12-dioxamyristic acid
  作者：Akira Katoh、Tianbao Lu、B. Devadas、Steven P. Adams、Jeffrey I. Gordon、George W. Gokel

  DOI：10.1021/jo00002a046

  日期：1991.1

  The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis. The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated. An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate. Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6% overall yield. The approach used is discussed along with the interesting chemistry of this system.