(R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-2-en-1-yloxy)propan-2-ol | 1164104-56-6

• 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-2-en-1-yloxy)propan-2-ol
• 英文别名: (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-[(E)-octadec-2-enoxy]propan-2-ol
• CAS: 1164104-56-6
• 化学式: C₃₇H₆₀O₃Si
• 分子量: 580.967
• InChiKey: LISVSFARPRTKCM-NYAGRQKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.98
• 重原子数：
  41
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-2-en-1-yloxy)propan-2-ol 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-1-en-1-yloxy)propan-2-ol
  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：

  (E)-2-十八烯醇 、 (R)-(tert-butyldiphenylsilyloxy)methyloxirane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到(R,E)-1-(tert-butyldiphenylsilyloxy)-3-(octadec-2-en-1-yloxy)propan-2-ol
  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

文献信息

• Synthesis and Antioxidant Properties of an Unnatural Plasmalogen Analogue Bearing a trans <i>O</i>-Vinyl Ether Linkage
  作者：Ravi S. Lankalapalli、Joseph T. Eckelkamp、Debajit Sircar、David A. Ford、Papasani V. Subbaiah、Robert Bittman

  DOI：10.1021/ol9009078

  日期：2009.7.2

  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.