(R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)prop-2-yl oleate | 1164104-59-9

• 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: (R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)prop-2-yl oleate
• CAS: 1164104-59-9
• 化学式: C₅₅H₉₂O₄Si
• 分子量: 845.419
• InChiKey: JHXHKTLNDASFPG-VSRABSAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.91
• 重原子数：
  60.0
• 可旋转键数：
  39.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)prop-2-yl oleate 在 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Antioxidant Properties of an Unnatural Plasmalogen Analogue Bearing a trans O-Vinyl Ether Linkage

  摘要：

  To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.

  DOI：

  10.1021/ol9009078
• 作为产物：
  描述：

  油酸 、 (R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)propan-2-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)prop-2-yl oleate
  参考文献：
  名称：

  Synthesis and Antioxidant Properties of an Unnatural Plasmalogen Analogue Bearing a trans O-Vinyl Ether Linkage

  摘要：

  To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.

  DOI：

  10.1021/ol9009078