[(2R)-3-hydroxy-2-octadec-9-enoyloxypropyl] octadec-9-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: [(2R)-3-hydroxy-2-octadec-9-enoyloxypropyl] octadec-9-enoate
• 化学式: C₃₉H₇₂O₅
• 分子量: 620.998
• InChiKey: AFSHUZFNMVJNKX-DIPNUNPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  44
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R)-3-hydroxy-2-octadec-9-enoyloxypropyl] octadec-9-enoate 、 甲苯磺酸胆碱 、 三氯氧磷 在 三乙胺 、 吡啶 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 [(2S)-2,3-di(octadec-9-enoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

  摘要：

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

  DOI：

  10.1021/jacs.5b05832
• 作为产物：
  描述：

  oleoyl chloride 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 [(2R)-3-hydroxy-2-octadec-9-enoyloxypropyl] octadec-9-enoate
  参考文献：
  名称：

  Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

  摘要：

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

  DOI：

  10.1021/jacs.5b05832