5-methyl-2-pentadecylfuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-methyl-2-pentadecylfuran
• 英文别名: 2-Methyl-5-pentadecylfuran
• 化学式: C₂₀H₃₆O
• 分子量: 292.505
• InChiKey: VFCMGCGLFDGYDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-2-pentadecylfuran 在 ruthenium trichloride 、 水 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 以67%的产率得到棕榈酸
  参考文献：
  名称：

  Synthesis and Tissue Biodistribution of [.omega.-11C]Palmitic Acid. A Novel Pet Imaging Agent for Cardiac Fatty acid Metabolism

  摘要：

  In order to diagnose patients with medium-chain acyl-CoA dehydrogenase deficiency with a noninvasive diagnostic technique such as positron emission tomography, we have developed a synthesis of [omega-C-11]palmitic acid. The radiochemical synthesis was achieved by coupling an alkylfuran Grignard reagent (7) with [C-11]methyl iodide, followed by rapid oxidative cleavage of the furan ring to the carboxylate using ruthenium tetraoxide. Tissue biodistribution studies in rats comparing [omega-C-11]palmitic acid and [1-C-11]palmitic acid show that the %ID/g and %ID/organ in the heart tissue after administration of [omega-C-11]palmitic acid is approximately 50% greater than after administration of[1-C-11]palmitic acid, due to the diminished metabolism of the [omega-C-11]palmitic acid. These studies show as well, low uptake in nontarget tissues (blood, lung, kidney, and muscle). PET images of a dog heart obtained after administration of [omega-C-11]- and [1-C-11]palmitic acid show virtually identical uptake and distribution in the myocardium. The differing cardiac washout of labeled palmitates measured by dynamic PET studies may allow diagnosis of disorders in cardiac fatty acid metabolism.

  DOI：

  10.1021/jm00041a028

文献信息

• Synthesis and Tissue Biodistribution of [.omega.-11C]Palmitic Acid. A Novel Pet Imaging Agent for Cardiac Fatty acid Metabolism
  作者：Brad O. Buckman、Henry F. VanBrocklin、Carmen S. Dence、Steven R. Bergmann、Michael J. Welch、John A. Katzenellenbogen

  DOI：10.1021/jm00041a028

  日期：1994.7

  In order to diagnose patients with medium-chain acyl-CoA dehydrogenase deficiency with a noninvasive diagnostic technique such as positron emission tomography, we have developed a synthesis of [omega-C-11]palmitic acid. The radiochemical synthesis was achieved by coupling an alkylfuran Grignard reagent (7) with [C-11]methyl iodide, followed by rapid oxidative cleavage of the furan ring to the carboxylate using ruthenium tetraoxide. Tissue biodistribution studies in rats comparing [omega-C-11]palmitic acid and [1-C-11]palmitic acid show that the %ID/g and %ID/organ in the heart tissue after administration of [omega-C-11]palmitic acid is approximately 50% greater than after administration of[1-C-11]palmitic acid, due to the diminished metabolism of the [omega-C-11]palmitic acid. These studies show as well, low uptake in nontarget tissues (blood, lung, kidney, and muscle). PET images of a dog heart obtained after administration of [omega-C-11]- and [1-C-11]palmitic acid show virtually identical uptake and distribution in the myocardium. The differing cardiac washout of labeled palmitates measured by dynamic PET studies may allow diagnosis of disorders in cardiac fatty acid metabolism.