15-iodo-tert-butyl-pentadecanoate | 191658-63-6

• 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: 15-iodo-tert-butyl-pentadecanoate
• 英文别名: Tert-butyl 15-iodopentadecanoate
• CAS: 191658-63-6
• 化学式: C₁₉H₃₇IO₂
• 分子量: 424.406
• InChiKey: QEYUIEREFBLLAI-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±18.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘甲烷-13C 、 15-iodo-tert-butyl-pentadecanoate 在 lithium(2-thienyl)iodocuprate 、 lithium dihydronaphthylide radical 、 三氟乙酸 作用下， 生成 棕榈酸-16-13C
  参考文献：
  名称：

  Synthesis of saturated fatty acids 11C(13C)-labelled in the ω-methyl position

  摘要：

  A method for the preparation of saturated fatty acids C-11 (C-13)-labelled in the omega-methyl position is described. A highly reactive zerovalent copper complex was prepared from lithium naphtalenide reduced lithium(2-thienyl)iodocuprate. The labelling precursors were obtained by addition of tert-butyl omega-iodocarboxylates to the organocuprate and these were reacted with [C-11]methyl iodide to form C-11-labelled.

  DOI：

  10.1002/(sici)1099-1344(199706)39:6<509::aid-jlcr996>3.0.co;2-h
• 作为产物：
  描述：

  15-溴十五酸 在 硫酸 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 53.0h， 生成 15-iodo-tert-butyl-pentadecanoate
  参考文献：
  名称：

  Synthesis of saturated fatty acids 11C(13C)-labelled in the ω-methyl position

  摘要：

  A method for the preparation of saturated fatty acids C-11 (C-13)-labelled in the omega-methyl position is described. A highly reactive zerovalent copper complex was prepared from lithium naphtalenide reduced lithium(2-thienyl)iodocuprate. The labelling precursors were obtained by addition of tert-butyl omega-iodocarboxylates to the organocuprate and these were reacted with [C-11]methyl iodide to form C-11-labelled.

  DOI：

  10.1002/(sici)1099-1344(199706)39:6<509::aid-jlcr996>3.0.co;2-h

文献信息

• Neu, H.; Kihlberg, T.; Langstroem, B., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 796 - 797
  作者：Neu, H.、Kihlberg, T.、Langstroem, B.

  DOI：——

  日期：——
• A new approach for the synthesis of [11C]-labeled fatty acids
  作者：F. Wüst、C. S. Dence、T. J. McCarthy、M. J. Welch

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

  日期：2000.11

  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.