1,12-bis(benzyloxy)dodecan-5-ol | 145475-41-8

• 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: 1,12-bis(benzyloxy)dodecan-5-ol
• 英文别名: 1,12-Bis(phenylmethoxy)dodecan-5-ol
• CAS: 145475-41-8
• 化学式: C₂₆H₃₈O₃
• 分子量: 398.586
• InChiKey: IWFCRBVGPJYAIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,12-bis(benzyloxy)dodecan-5-ol 在 吡啶 、 溴 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 3.3h， 生成 5-bromododecane-1,12-diol
  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
• 作为产物：
  描述：

  4-溴丁醚苄酯 、 8-(benzyloxy)octanal 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 生成 1,12-bis(benzyloxy)dodecan-5-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

文献信息

• Synthesis and use of the n-bromododecane-1,12-diols as conformational probes for general anesthetic target sites
  作者：R. Dickinson、E. H. Smith、N. P. Franks、W. R. Lieb

  DOI：10.1021/jm00053a014

  日期：1993.1

  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.