octadecane-2,7,12,17-tetraol

• 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: octadecane-2,7,12,17-tetraol
• 英文别名: 2,7,12,17-Octadecanetetrol；octadecane-2,7,12,17-tetrol
• 化学式: C₁₈H₃₈O₄
• 分子量: 318.497
• InChiKey: AYWPXIDLJPKHIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,6-(2,2'-dithienyl)-1,6-bis(trimethylsilyloxy)hexane 在 正丁基锂 、 镍 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 为溶剂， 反应 4.0h， 生成 octadecane-2,7,12,17-tetraol
  参考文献：
  名称：

  Anesthetic Potency of Two Novel Synthetic Polyhydric Alkanols Longer than the n-Alkanol Cutoff:  Evidence for a Bilayer-Mediated Mechanism of Anesthesia?

  摘要：

  The polyhydroxyalkanes 1,6,11,16-hexadecanetetraol (1) and 2,7,12,17-octadecanetetraol (2) were synthesized utilizing the thiophene ring as a scaffold to affix the hydroxyalkyl chains by lithiation of the acidic alpha-hydrogens and subsequent desulfurization. Both compounds exhibited significant anesthetic potency, individually and in additivity studies with hexanol, using immobility in tadpoles as the phenotypic endpoint. These results, which contradict a protein-binding mechanism in which cutoff results from steric hindrance, are consistent with recent predictions of a membrane-mediated mechanism involving the lateral pressure profile.

  DOI：

  10.1021/jm049459k

文献信息

• Anesthetic Potency of Two Novel Synthetic Polyhydric Alkanols Longer than the <i>n</i>-Alkanol Cutoff:  Evidence for a Bilayer-Mediated Mechanism of Anesthesia?
  作者：Justin T. Mohr、Gordon W. Gribble、Susan S. Lin、Roderic G. Eckenhoff、Robert S. Cantor

  DOI：10.1021/jm049459k

  日期：2005.6.1

  The polyhydroxyalkanes 1,6,11,16-hexadecanetetraol (1) and 2,7,12,17-octadecanetetraol (2) were synthesized utilizing the thiophene ring as a scaffold to affix the hydroxyalkyl chains by lithiation of the acidic alpha-hydrogens and subsequent desulfurization. Both compounds exhibited significant anesthetic potency, individually and in additivity studies with hexanol, using immobility in tadpoles as the phenotypic endpoint. These results, which contradict a protein-binding mechanism in which cutoff results from steric hindrance, are consistent with recent predictions of a membrane-mediated mechanism involving the lateral pressure profile.