6-[4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]phenyl]hexan-1-ol | 1261552-53-7

• 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: 6-[4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]phenyl]hexan-1-ol
• CAS: 1261552-53-7
• 化学式: C₂₄H₂₈O
• 分子量: 332.486
• InChiKey: ORPNWVYOMILTTR-RNVGXFRSSA-N

物化性质

• 沸点：
  531.4±39.0 °C(predicted)
• 密度：
  1.031±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  6-[4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]phenyl]hexan-1-ol 、 2-氯-2-氧-1,3,2-二氧磷杂环戊烷 、 三甲胺 以 乙腈 为溶剂， 反应 7.0h， 以17%的产率得到6-(4-((1E,3E,5E)-6-phenylhexa-1,3,5-trien-1-yl)phenyl)hexyl (2-(trimethylammonio)ethyl) phosphate
  参考文献：
  名称：

  Synthesis and spectral properties of fluorescent linear alkylphosphocholines labeled with all-(E)-1,6-diphenyl-1,3,5-hexatriene

  摘要：

  A synthetic method has been designed to produce alkylphosphantidylcholine lipid molecules with the fluorescent group all-(E)-1 6-diphenyl-1 3 5-hexatriene (DPH) incorporated to the end of a polymethylene chain of variable length The resulting compounds may be viewed as single-chain fluorescent lipid probes terminated with a phosphocholine (PHC) polar head-group The method was applied to the synthesis of two lipids with different alkyl chain length PHC-C4-DPH (1) and PHC-C6-DPH (2) as well as the corresponding alcohols OH-C4-DPH (8) and OH-C6-DPH (9) The absorption and fluorescence properties of these compounds in fluid solution were very similar to those of the well-known lipid probe propionic acid-DPH (PA-DPH) In addition it was observed that the alkylphosphocholines were easily incorporated into unilamellar lipid vesicles in which the DPH group would be positioned most likely near the centre of the bilayer In these conditions 1 shows a fluorescence quantum yield of 0 4 +/- 0 1 and a relatively simple decay time with tau(av), close to 5 0 ns Fluorescence polarization experiments also indicate that the reorientational motions of the DPH group of phosphocholine 1 are sensitive to the fluidity changes that accompany the main thermal phase transition of the bilayer As a result both compounds may be of utility as novel fluorescent lipid probes characterized by a biomimetic zwitterionic polar head-group (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.010
• 作为产物：
  描述：

  tert-butyldimethyl((6-(4-((1E,3E,5E)-6-phenylhexa-1,3,5-trien-1-yl)phenyl)hexyl)oxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以97%的产率得到6-[4-[(1E,3E,5E)-6-phenylhexa-1,3,5-trienyl]phenyl]hexan-1-ol
  参考文献：
  名称：

  Synthesis and spectral properties of fluorescent linear alkylphosphocholines labeled with all-(E)-1,6-diphenyl-1,3,5-hexatriene

  摘要：

  A synthetic method has been designed to produce alkylphosphantidylcholine lipid molecules with the fluorescent group all-(E)-1 6-diphenyl-1 3 5-hexatriene (DPH) incorporated to the end of a polymethylene chain of variable length The resulting compounds may be viewed as single-chain fluorescent lipid probes terminated with a phosphocholine (PHC) polar head-group The method was applied to the synthesis of two lipids with different alkyl chain length PHC-C4-DPH (1) and PHC-C6-DPH (2) as well as the corresponding alcohols OH-C4-DPH (8) and OH-C6-DPH (9) The absorption and fluorescence properties of these compounds in fluid solution were very similar to those of the well-known lipid probe propionic acid-DPH (PA-DPH) In addition it was observed that the alkylphosphocholines were easily incorporated into unilamellar lipid vesicles in which the DPH group would be positioned most likely near the centre of the bilayer In these conditions 1 shows a fluorescence quantum yield of 0 4 +/- 0 1 and a relatively simple decay time with tau(av), close to 5 0 ns Fluorescence polarization experiments also indicate that the reorientational motions of the DPH group of phosphocholine 1 are sensitive to the fluidity changes that accompany the main thermal phase transition of the bilayer As a result both compounds may be of utility as novel fluorescent lipid probes characterized by a biomimetic zwitterionic polar head-group (C) 2010 Elsevier B V All rights reserved

  DOI：

  10.1016/j.jphotochem.2010.09.010