(R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl ester | 775341-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl ester
• CAS: 775341-89-4
• 化学式: C₂₉H₄₃BrO₆
• 分子量: 567.561
• InChiKey: CJAZFXNFTMTDDC-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  36.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl ester 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以98%的产率得到(R)-3-levulinoyloxyhexadecanoic 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：

  乙酰丙酸 、 2-(4-bromophenyl)-2-oxoethyl (R)-3-hydroxyhexadecanoate 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， 反应 3.0h， 以96%的产率得到(R)-3-(levulinoyloxy)hexadecanoic acid 2-(4-bromophenyl)-2-oxoethyl 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