dodeca-1,11-dien-6-ol | 145475-48-5

• 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: dodeca-1,11-dien-6-ol
• CAS: 145475-48-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: PDKDECDFYMDFSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dodeca-1,11-dien-6-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 生成 [(E)-7-[(3Z)-3-(3-methoxyprop-1-en-2-yl)-2,2-diphenyl-5,6,7,8-tetrahydrooxasilocin-8-yl]hept-2-enyl] acetate
  参考文献：
  名称：

  基团选择性闭环烯炔复分解：炔基甲硅烷氧基系链二烯的浓度依赖性选择性曲线

  摘要：

  使用 Grubbs 第一代和第二代催化剂实现了炔基甲硅烷氧基系链二炔的高基团选择性闭环复分解反应。在几乎相同的空间和立体电子环境中，在较高浓度下区分两个烯烃部分的显着选择性增加被认为是在生成的两种亚烷基物质快速预平衡下形成较小尺寸环的闭环率较高的结果来自任一烯烃部分。

  DOI：

  10.1021/ja046043n
• 作为产物：
  描述：

  5-己烯-1-醇 在 magnesium 、 pyridinium chlorochromate 作用下， 以 乙醚 为溶剂， 生成 dodeca-1,11-dien-6-ol
  参考文献：
  名称：

  Synthesis and use of the n-bromododecane-1,12-diols as conformational probes for general anesthetic target sites

  摘要：

  The n-bromododecane-1,12-diols with bromine on carbons 2,3,5, and 6, respectively, were synthesized and found to be potent general anesthetics. They were also found to be potent inhibitors of firefly luciferase, a protein model for the primary target sites underlying general anesthesia. However, their effects on lipid bilayers were small, lowering the chain-melting phase transition temperature by less than l-degrees-C at their EC50 concentrations for general anesthesia. A large dependence upon the position of the bromine atom was found for both n-hexadecane/water partition coefficients and inhibition constants for firefly luciferase; a much smaller positional dependence was found for induction of general anesthesia and for disrupting lipids. These results are consistent with the bulky bromine atom inhibiting the conformational flexibility of the diol hydrocarbon chain, making these bromo diols useful probes for ascertaining the shapes of apolar binding sites. In particular, our measurements suggest that these novel anesthetics produce general anesthesia by binding to long and relatively narrow apolar target sites in the central nervous system.

  DOI：

  10.1021/jm00053a014