(E)-4-Oxo-hept-2-enedioic acid 7-{(R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl} ester | 590386-54-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: (E)-4-Oxo-hept-2-enedioic acid 7-{(R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl} ester
• CAS: 590386-54-2
• 化学式: C₃₃H₅₈NO₁₃P
• 分子量: 707.796
• InChiKey: QBXFHNPCGLBYNQ-HFRCXCCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  48.0
• 可旋转键数：
  29.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  201.06
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (E)-4-Oxo-hept-2-enedioic acid 7-{(R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl} ester 在 三氟乙酸 作用下， 反应 24.0h， 以100%的产率得到(E)-4-Oxo-hept-2-enedioic acid 7-{(R)-2-[(2-amino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl} ester
  参考文献：
  名称：

  Total Syntheses of Bioactive Oxidized Ethanolamine Phospholipids

  摘要：

  GraphicsTruncated ethanolamine phospholipids containing aldehyde functionality, e.g. OVPE, and the corresponding acids, are generated by oxidative cleavage of polyunsaturated phospholipids. To confirm their identities and facilitate studies of the chemistry and biological actions of these analogues of biologically active phosphatidylcholines, e.g. OVPC, total syntheses were developed. An efficient general strategy was used that features selective N-protection of 2-lysophosphatidylethanolamine, and generation of the target compounds by mild deprotection of stable precursors.

  DOI：

  10.1021/ol034729z
• 作为产物：
  描述：

  3(2-呋喃)丙酸 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 为溶剂， 反应 81.0h， 生成 (E)-4-Oxo-hept-2-enedioic acid 7-{(R)-2-[(2-tert-butoxycarbonylamino-ethoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl} ester
  参考文献：
  名称：

  Total Syntheses of Bioactive Oxidized Ethanolamine Phospholipids

  摘要：

  GraphicsTruncated ethanolamine phospholipids containing aldehyde functionality, e.g. OVPE, and the corresponding acids, are generated by oxidative cleavage of polyunsaturated phospholipids. To confirm their identities and facilitate studies of the chemistry and biological actions of these analogues of biologically active phosphatidylcholines, e.g. OVPC, total syntheses were developed. An efficient general strategy was used that features selective N-protection of 2-lysophosphatidylethanolamine, and generation of the target compounds by mild deprotection of stable precursors.

  DOI：

  10.1021/ol034729z