4-hydroxy-1-[(tetrahydropyran-2-yl)oxy]decane | 1190596-19-0

• 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: 4-hydroxy-1-[(tetrahydropyran-2-yl)oxy]decane
• CAS: 1190596-19-0
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: MNYNIJBHEKCQJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-[(tetrahydropyran-2-yl)oxy]decane 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到4-methoxy-1-[(tetrahydropyran-2-yl)oxy]decane
  参考文献：
  名称：

  The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid

  摘要：

  The hitherto unknown (+/-)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mu M) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.074
• 作为产物：
  描述：

  4,5-epoxy-1-[(tetrahydropyran-2-yl)oxy]pentane 、 正戊基溴化镁 在 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到4-hydroxy-1-[(tetrahydropyran-2-yl)oxy]decane
  参考文献：
  名称：

  The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid

  摘要：

  The hitherto unknown (+/-)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mu M) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.074