methyl 7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoate | 264874-79-5

• 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: methyl 7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoate
• CAS: 264874-79-5
• 化学式: C₂₄H₃₂O₃Si
• 分子量: 396.602
• InChiKey: PYTKHJFDSXCONG-NSIKDUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoate 在 4-甲氨基吡啶 、 lithium hydroxide 、 四丁基氟化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 96.0h， 生成 1-octadecanoyl-2-[7-hydroxyhept-5(Z)-enoyl]-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Analysis of oxidized glycerophosphocholine lipids using electrospray ionization mass spectrometry and microderivatization techniques

  摘要：

  Oxidized low-density lipoprotein (LDL) is thought to play an important role in atherogenesis and cardiovascular disease in humans. Oxidized LDL is a complex mixture of many oxidized species, including numerous oxidized glycerophospholipids. Electrospray ionization and tandem mass spectrometry as well as microchemical derivatization of high-performance liquid chromatographically purified fractions derived from oxidized LDL were investigated as means to determine the structure of individual components present in oxidized LDL. One major oxidized phosphocholine lipid had an [M + H](+) ion at m/z 650. Derivatization to the trimethylsilyl ether and methoxime caused shifts in mass which, along with negative ion collision-induced dissociation mass spectra, were consistent with the presence of three species, 1-palmitoyl-2-(9-oxononanoyl)glycerophosphocholine and two isomeric 1-octadecanoyl-2-(hydroxyheptenoyl)glycerophosphocholines. These species were chemically synthesized. Trimethylsilylation of free hydroxyl groups increased the mass of the phospholipid acyl chains containing hydroxyl groups by 72 u. Conversion of carbonyl groups to the methoxylamine derivative increased the mass by 29 u. Ozonolysis of those products which contained double bonds proved to be a facile technique to determine the position and number of double bonds present. The use of these techniques was illustrated in the structural characterization of one major component (m/z 650, positive ions) in oxidized LDL as 1-octadecanoyl-2-(7-hydroxy-hepta-5-enoyl)glycerophosphocholine. A possible mechanism for the formation of this unique chain-shortened glycerophospholipid is proposed. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1096-9888(200002)35:2<224::aid-jms933>3.0.co;2-g
• 作为产物：
  描述：

  7-Hydroxy-5-heptynoic Acid 在 nickel diacetate 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氢气 、 乙二胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 methyl 7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoate
  参考文献：
  名称：

  Analysis of oxidized glycerophosphocholine lipids using electrospray ionization mass spectrometry and microderivatization techniques

  摘要：

  Oxidized low-density lipoprotein (LDL) is thought to play an important role in atherogenesis and cardiovascular disease in humans. Oxidized LDL is a complex mixture of many oxidized species, including numerous oxidized glycerophospholipids. Electrospray ionization and tandem mass spectrometry as well as microchemical derivatization of high-performance liquid chromatographically purified fractions derived from oxidized LDL were investigated as means to determine the structure of individual components present in oxidized LDL. One major oxidized phosphocholine lipid had an [M + H](+) ion at m/z 650. Derivatization to the trimethylsilyl ether and methoxime caused shifts in mass which, along with negative ion collision-induced dissociation mass spectra, were consistent with the presence of three species, 1-palmitoyl-2-(9-oxononanoyl)glycerophosphocholine and two isomeric 1-octadecanoyl-2-(hydroxyheptenoyl)glycerophosphocholines. These species were chemically synthesized. Trimethylsilylation of free hydroxyl groups increased the mass of the phospholipid acyl chains containing hydroxyl groups by 72 u. Conversion of carbonyl groups to the methoxylamine derivative increased the mass by 29 u. Ozonolysis of those products which contained double bonds proved to be a facile technique to determine the position and number of double bonds present. The use of these techniques was illustrated in the structural characterization of one major component (m/z 650, positive ions) in oxidized LDL as 1-octadecanoyl-2-(7-hydroxy-hepta-5-enoyl)glycerophosphocholine. A possible mechanism for the formation of this unique chain-shortened glycerophospholipid is proposed. Copyright (C) 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1096-9888(200002)35:2<224::aid-jms933>3.0.co;2-g