27-benzyloxy-octacosanoic acid methyl ester | 775341-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 27-benzyloxy-octacosanoic acid methyl ester
• 英文别名: Methyl 27-phenylmethoxyoctacosanoate
• CAS: 775341-74-7
• 化学式: C₃₆H₆₄O₃
• 分子量: 544.902
• InChiKey: BBTGLPSHDMXHCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  595.2±23.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  39
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  27-benzyloxy-octacosanoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以82%的产率得到27-benzyloxy-octacosanoic acid
  参考文献：
  名称：

  Preparation of a Lipid A Derivative That Contains a 27-Hydroxyoctacosanoic Acid Moiety

  摘要：

  A general synthetic strategy for long-chain omega-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between omega-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for the preparation of lipid A derivatives of Rhizobium sin-1, which have the ability to inhibit the E. coli LPS-dependent synthesis of tumor necrosis factor by human monocytes.

  DOI：

  10.1021/ol048746f
• 作为产物：
  描述：

  Methyl hexacos-25-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Rh/Al₂O₃ 三乙基硅烷 、 六甲基二硅氧烷 、 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 27-benzyloxy-octacosanoic acid methyl ester
  参考文献：
  名称：

  Preparation of a Lipid A Derivative That Contains a 27-Hydroxyoctacosanoic Acid Moiety

  摘要：

  A general synthetic strategy for long-chain omega-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between omega-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for the preparation of lipid A derivatives of Rhizobium sin-1, which have the ability to inhibit the E. coli LPS-dependent synthesis of tumor necrosis factor by human monocytes.

  DOI：

  10.1021/ol048746f

文献信息

• Preparation of a Lipid A Derivative That Contains a 27-Hydroxyoctacosanoic Acid Moiety
  作者：Balaji Santhanam、Geert-Jan Boons

  DOI：10.1021/ol048746f

  日期：2004.9.1

  A general synthetic strategy for long-chain omega-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between omega-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for the preparation of lipid A derivatives of Rhizobium sin-1, which have the ability to inhibit the E. coli LPS-dependent synthesis of tumor necrosis factor by human monocytes.