14-碘十四烷酸 | 71736-21-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 14-碘十四烷酸
• 英文名称: 14-iodo-tetradecanoic acid
• 英文别名: 14-Iodotetradecanoic acid
• CAS: 71736-21-5
• 化学式: C₁₄H₂₇IO₂
• 分子量: 354.272
• InChiKey: PGUIWAWDJYGLBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  14-碘十四烷酸 在 silver perchlorate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 84.0h， 生成 1-氧杂环十五烷-2-酮
  参考文献：
  名称：

  Intramolecular cyclization of (.omega.-carboxyalkyl)sulfonium salts. A novel synthesis of macrocyclic lactones

  摘要：

  DOI：

  10.1021/jo00283a010
• 作为产物：
  描述：

  1,12-二碘十二烷 在 氢碘酸 、 sodium 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 14-碘十四烷酸
  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

文献信息

• Novel Synthesis of Macrocyclic Lactones from ω-Carboxyalkylsulfonium Salts
  作者：Haruo Matsuyama、Takako Nakamura、Akinori Takatsuka、Michio Kobayashi、Nobumasa Kamigata

  DOI：10.1246/cl.1988.1931

  日期：1988.11.5

  An intramolecular cyclization of S-(ω-carboxyalkyl)thiolanium salts took place readily under weakly basic conditions to afford sulfur-containing macrocyclic lactones in good yields.

  S-(ω-羧基烷基)硫醇盐的分子内环化在弱碱性条件下很容易发生，以良好的产率得到含硫大环内酯。
• Hunsdiecker; Hunsdiecker, Chemische Berichte, 1942, vol. 75, p. 294
  作者：Hunsdiecker、Hunsdiecker

  DOI：——

  日期：——
• Preparation of macrocyclic lactones by ring closure of cesium carboxylates
  作者：Wim H. Kruizinga、Richard M. Kellogg

  DOI：10.1021/ja00407a039

  日期：1981.8
• Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice, Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55
  作者：Riche, Francoise、Mathieu, Jean-Paul、Vincens, Maurice、Bardy, Andre、Comet, Michel、Vidal, Michel

  DOI：——

  日期：——
• MATSUYAMA, HARUO;NAKAMURA, TAKAKO;TAKATSUKA, AKINORI;KOBAYASHI, MICHIO;KA+, CHEM. LETT.,(1988) N1, C. 1931-1932
  作者：MATSUYAMA, HARUO、NAKAMURA, TAKAKO、TAKATSUKA, AKINORI、KOBAYASHI, MICHIO、KA+

  DOI：——

  日期：——