11-(1,1'-biphenyl-4-yloxy)-1-undecanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 11-(1,1'-biphenyl-4-yloxy)-1-undecanol
• 英文别名: 11-(4-Phenylphenoxy)undecan-1-ol；11-(4-phenylphenoxy)undecan-1-ol
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: ATGADUQINJFANC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-(1,1'-biphenyl-4-yloxy)-1-undecanol 在 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以27%的产率得到1,1'-biphenyl-4-yl 11-bromoundecyl ether
  参考文献：
  名称：

  Electrochemical release from gold–thiolate electrodes for controlled insertion of ion channels into bilayer membranes

  摘要：

  A proof-of-principle experiment to inject a sub-attomole amount of a channel compound into a bilayer membrane is described. The system is based on reductive cleavage of a self-assembled gold-thiol monolayer. In 'macroscopic' experiments, 11-biphenyloxyundecane thiol formed well-ordered monolayers by open-circuit or controlled potential deposition. The products of reductive release were determined by chromatographic analysis. In DMF, the sole reduction product is the corresponding disulfide. In acetonitrile and water, only the thiol is detected. The current efficiency is low due to competing electrolysis of water, and to the low solubility of the released thiol or disulfide layer. On a 'microscopic' scale, the half ester of dithiodibutyric acid with gramicidin was deposited on a gold microelectrode under open circuit conditions. The thoroughly washed microelectrode, placed in proximity to a bilayer, released gramicidin only following a 100 ins pulse of reducing potential. The transfer efficiency of this method for controlled positioning of ion channels is estimated to be better than 1 part in 10(5). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.06.004
• 作为产物：
  描述：

  11-溴-1-十一醇 、 对羟基联苯 在 氢氧化钾 作用下， 以 水 、 叔丁醇 为溶剂， 反应 3.0h， 以68%的产率得到11-(1,1'-biphenyl-4-yloxy)-1-undecanol
  参考文献：
  名称：

  Electrochemical release from gold–thiolate electrodes for controlled insertion of ion channels into bilayer membranes

  摘要：

  A proof-of-principle experiment to inject a sub-attomole amount of a channel compound into a bilayer membrane is described. The system is based on reductive cleavage of a self-assembled gold-thiol monolayer. In 'macroscopic' experiments, 11-biphenyloxyundecane thiol formed well-ordered monolayers by open-circuit or controlled potential deposition. The products of reductive release were determined by chromatographic analysis. In DMF, the sole reduction product is the corresponding disulfide. In acetonitrile and water, only the thiol is detected. The current efficiency is low due to competing electrolysis of water, and to the low solubility of the released thiol or disulfide layer. On a 'microscopic' scale, the half ester of dithiodibutyric acid with gramicidin was deposited on a gold microelectrode under open circuit conditions. The thoroughly washed microelectrode, placed in proximity to a bilayer, released gramicidin only following a 100 ins pulse of reducing potential. The transfer efficiency of this method for controlled positioning of ion channels is estimated to be better than 1 part in 10(5). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.06.004

文献信息

• Electrochemical release from gold–thiolate electrodes for controlled insertion of ion channels into bilayer membranes
  作者：M.B Buchmann、T.M Fyles、T Sutherland

  DOI：10.1016/j.bmc.2003.06.004

  日期：2004.3

  A proof-of-principle experiment to inject a sub-attomole amount of a channel compound into a bilayer membrane is described. The system is based on reductive cleavage of a self-assembled gold-thiol monolayer. In 'macroscopic' experiments, 11-biphenyloxyundecane thiol formed well-ordered monolayers by open-circuit or controlled potential deposition. The products of reductive release were determined by chromatographic analysis. In DMF, the sole reduction product is the corresponding disulfide. In acetonitrile and water, only the thiol is detected. The current efficiency is low due to competing electrolysis of water, and to the low solubility of the released thiol or disulfide layer. On a 'microscopic' scale, the half ester of dithiodibutyric acid with gramicidin was deposited on a gold microelectrode under open circuit conditions. The thoroughly washed microelectrode, placed in proximity to a bilayer, released gramicidin only following a 100 ins pulse of reducing potential. The transfer efficiency of this method for controlled positioning of ion channels is estimated to be better than 1 part in 10(5). (C) 2003 Elsevier Ltd. All rights reserved.