12-iodo-dodecylmalonic acid diethyl ester | 320750-60-5

• 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: 12-iodo-dodecylmalonic acid diethyl ester
• 英文别名: Diethyl 2-(12-iodododecyl)propanedioate
• CAS: 320750-60-5
• 化学式: C₁₉H₃₅IO₄
• 分子量: 454.389
• InChiKey: BVNMUBVLSBAZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-iodo-dodecylmalonic acid diethyl ester 在 氢碘酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 15-iodo-tert-butyl-tetradecanoate
  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
• 作为产物：
  描述：

  1,12-二溴十二烷 在 sodium 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.5h， 生成 12-iodo-dodecylmalonic acid diethyl ester
  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