rac-2-O-ethyl-1-O-methylthiomethyl-3-O-octadecylglycerol | 166824-13-1

• 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: rac-2-O-ethyl-1-O-methylthiomethyl-3-O-octadecylglycerol
• 英文别名: rac-1-O-octadecyl-2-O-ethyl-3-O-methylthiomethylglycerol；1-{2-Ethoxy-3-[(methylsulfanyl)methoxy]propoxy}octadecane；1-[2-ethoxy-3-(methylsulfanylmethoxy)propoxy]octadecane
• CAS: 166824-13-1
• 化学式: C₂₅H₅₂O₃S
• 分子量: 432.752
• InChiKey: SFUWTUJVHKQFNC-UHFFFAOYSA-N

物化性质

• 沸点：
  503.9±45.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  29
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-2-O-ethyl-1-O-methylthiomethyl-3-O-octadecylglycerol 在 2,6-二甲基吡啶 、 氢氧化钾 、 溴 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 rac-2-O-ethyl-1-O-[2-(2-hydroxyethylthio)ethoxy]methyl-3-O-octadecylglycerol
  参考文献：
  名称：

  Synthesis of alkyl-type functionalised glycerolipids from methylthiomethyl ethers

  摘要：

  The synthesis of alkyl-type glycerolipids containing functional groups in the polar domain from methylthiomethyl ethers is described.

  DOI：

  10.1070/mc2005v015n01abeh001947
• 作为产物：
  描述：

  rac-1-O-octadecyl-2-O-ethylglycerol 、 二甲基亚砜 在 乙酸酐 、 溶剂黄146 作用下， 以 苯 为溶剂， 以50%的产率得到rac-2-O-ethyl-1-O-methylthiomethyl-3-O-octadecylglycerol
  参考文献：
  名称：

  摘要：

  Cationic ether lipids; containing nitrogenous heterocyclic bases as the positively charged groups were synthesized. Treatment of methylthiomethyl ethers of dialkylglycerols with bromine afforded highly reactive alpha-bromo ethers. These products reacted with various nucleophilic reagents giving rise to a series of cationic alkylglycerols.

  DOI：

  10.1023/a:1021325223619

文献信息

• Synthesis of new alkyl-type glycerolipids from methylthiomethyl ethers
  作者：N. V. Plyavnik、M. A. Maslov、G. A. Serebrennikova

  DOI：10.1007/s11172-008-0298-y

  日期：2008.10

  The synthesis of alkyl-type glycerolipids with aliphatic and heterocyclic cationic “heads” separated by an acetal spacer from the glycerol core is described. The synthesis of sulfur-containing glycerolipids with an ether bond from rac-1-O-(2-bromoethoxy)methyl-2-O-ethyl-3-O-octadecylglycerol and functionalized thiols is considered.

  介绍了脂肪族和杂环族阳离子 "头 "与甘油核心之间由缩醛间隔物隔开的烷基型甘油酯的合成。研究还考虑了由 rac-1-O-(2-溴乙氧基)甲基-2-O-乙基-3-O-十八烷基甘油和功能化硫醇合成具有醚键的含硫甘油酯。
• Konstantinova, I. D.; Zavgorodnii, S. G.; Miroshnikov, A. I., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 1, p. 58 - 61
  作者：Konstantinova, I. D.、Zavgorodnii, S. G.、Miroshnikov, A. I.、Ushakova, I. P.、Serebrennikova, G. A.

  DOI：——

  日期：——
• Synthesis of alkyl-type functionalised glycerolipids from methylthiomethyl ethers
  作者：Natalya V. Plyavnik、Mikhail A. Maslov、Galina A. Serebrennikova

  DOI：10.1070/mc2005v015n01abeh001947

  日期：2005.1

  The synthesis of alkyl-type glycerolipids containing functional groups in the polar domain from methylthiomethyl ethers is described.
• ——
  作者：M. A. Maslov、N. G. Morozova、G. A. Serebrennikova

  DOI：10.1023/a:1021325223619

  日期：——

  Cationic ether lipids; containing nitrogenous heterocyclic bases as the positively charged groups were synthesized. Treatment of methylthiomethyl ethers of dialkylglycerols with bromine afforded highly reactive alpha-bromo ethers. These products reacted with various nucleophilic reagents giving rise to a series of cationic alkylglycerols.