1,6-(2,2'-dithienyl)-1,6-bis(trimethylsilyloxy)hexane | 854439-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,6-(2,2'-dithienyl)-1,6-bis(trimethylsilyloxy)hexane
• 英文别名: (1,6-Dithiophen-2-yl-6-trimethylsilyloxyhexoxy)-trimethylsilane
• CAS: 854439-82-0
• 化学式: C₂₀H₃₄O₂S₂Si₂
• 分子量: 426.792
• InChiKey: OUMNVXRUYLDOOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  三甲基氯硅烷 、 1,6-(2,2'-dithienyl)hexane-1,6-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,6-(2,2'-dithienyl)-1,6-bis(trimethylsilyloxy)hexane
  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