ω-1-[11C]palmitic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ω-1-[11C]palmitic acid
• 英文别名: (1511C)hexadecanoic acid
• 化学式: C₁₆H₃₂O₂
• 分子量: 255.418
• InChiKey: IPCSVZSSVZVIGE-JVVVGQRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 ω-1-[11C]palmitic acid
  参考文献：
  名称：

  A new approach for the synthesis of [11C]-labeled fatty acids

  摘要：

  The synthesis of omega-[C-11], omega -1-[C-11] and omega -3-[C-11:] palmitic acid employing a cross-coupling reaction between a functionalized copper-zinc reagent with [C-11]Mel, [1-C-11]EtI and [1-C-11]BuI is described. A tert.-butyl-protected omega -iodo fatty acid precursor (BuO2C)-Bu-t-(CH2)n-I (n = 11, 13, 14) was converted into the corresponding dialkylzinc reagent [(BuO2C)-Bu-t-(CH2)(n)](2)Zn which reacts with Me2CuI(MgCl)(2) to give a highly reactive copper reagent [(BuO2C)-Bu-t-(CH2)(N)](2)CuI(MgCl)(2)Me2Zn as the labeling precursor. The cross-coupling reaction with [C-11]MeI, [1-C-11:]EB and [1-C-11]BuI provided the protected palmitic acid, specifically labeled with carbon-11 in several positions. The corresponding carbon-13 labeled compounds were synthesized to verify the labeling position. In a typical synthesis with [1-C-11]EtI starting with 250 mCi of [C-11]CO2, 14 mCi (6% decay-corrected based on [C-11]CO2) of omega -1-[C-11]palmitic acid was obtained within 30 minutes after EOB in 88% radiochemical purity prior to purification by HPLC. The general feature of this approach allows the convenient synthesis of palmitic acid specifically labeled in the omega, omega -1 or omega -3 positions by using several [C-11]-labeled alkyl iodides ([C-11]MeI, [1-C-11]EtI or [1-C-11]BuI) in the same cross-coupling protocol.

  DOI：

  10.1002/1099-1344(200011)43:13<1289::aid-jlcr420>3.0.co;2-q