ethyl 2,2-difluorododecanoate | 502497-40-7

• 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: ethyl 2,2-difluorododecanoate
• 英文别名: Dodecanoic acid, 2,2-difluoro-, ethyl ester
• CAS: 502497-40-7
• 化学式: C₁₄H₂₆F₂O₂
• 分子量: 264.356
• InChiKey: BOGFKPNSGGDEIF-UHFFFAOYSA-N

物化性质

• 沸点：
  290.9±25.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluorododecanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71%的产率得到α,α-difluorododecanoic acid
  参考文献：
  名称：

  Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate

  摘要：

  在我们之前的工作中，乙基溴二氟乙酸酯（1）在Cu粉的存在下与由电子吸引基团激活的烯烃反应，通过阴离子中间体形成Michael型加合物。发现使用未激活的烯烃进行相同反应会通过自由基机理形成加成产物。α-甲基苯乙烯的自由基中间体由苯环稳定并产生新的二聚产物。这种反应与1-癸烯提供了制备2,2-二氟十二酸的便捷途径。

  DOI：

  10.1135/cccc20021285
• 作为产物：
  描述：

  2-decyl-2-ethoxycarbonyl-1,3-dithiane 在 三氟化溴 作用下， 以 一氟三氯甲烷 为溶剂， 生成 ethyl 2,2-difluorododecanoate
  参考文献：
  名称：

  A Novel Method for the Preparation of α,α‘-Difluoroesters and Acids Using BrF₃

  摘要：

  Alkyl-, haloalkyl-, and ketoalkyl-2-ethoxycarbonyl-1,3-dithianes were easily made from the appropriate primary or secondary alkyl bromides, 1,3-dithiane, and ethyl chloroformate. They were reacted with BrF3 to form the corresponding alpha,alpha-difluoro esters in 65-75% yield. Reaction conditions are very mild (1-2 min, 0 degreesC). The two sulfur atoms of the dithiane are essential for the reaction.

  DOI：

  10.1021/jo034829i

文献信息

• Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate
  作者：Kazuyuki Sato、Yuko Ogawa、Misato Tamura、Mika Harada、Terumasa Ohara、Masaaki Omote、Akira Ando、Itsumaro Kumadaki

  DOI：10.1135/cccc20021285

  日期：——

  In our previous work, reaction of ethyl bromodifluoroacetate (1) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a radical mechanism. The radical intermediate from α-methylstyrene was stabilized by a benzene ring and gave novel dimerization products. This reaction with 1-decene provided a convenient route to 2,2-difluorododecanoic acid.

  在我们之前的工作中，乙基溴二氟乙酸酯（1）在Cu粉的存在下与由电子吸引基团激活的烯烃反应，通过阴离子中间体形成Michael型加合物。发现使用未激活的烯烃进行相同反应会通过自由基机理形成加成产物。α-甲基苯乙烯的自由基中间体由苯环稳定并产生新的二聚产物。这种反应与1-癸烯提供了制备2,2-二氟十二酸的便捷途径。
• Metal-Free Visible Light Hydroperfluoroalkylation of Unactivated Alkenes Using Perfluoroalkyl Bromides
  作者：Tomoko Yajima、Satsuki Shigenaga

  DOI：10.1021/acs.orglett.8b03596

  日期：2019.1.4

  Organic dye-catalyzed visible light induced hydroperfluoroalkylation of unactivated alkenes is described. Hydroperfluoroalkylation proceeds selectively and is applicable for various perfluoroalkyl bromide and alkenes including internal alkenes. The reaction mechanism is discussed, and it is shown that the hydrogen source varies with reaction conditions.
• A Novel Method for the Preparation of α,α‘-Difluoroesters and Acids Using BrF₃
  作者：Aviv Hagooly、Revital Sasson、Shlomo Rozen

  DOI：10.1021/jo034829i

  日期：2003.10.1

  Alkyl-, haloalkyl-, and ketoalkyl-2-ethoxycarbonyl-1,3-dithianes were easily made from the appropriate primary or secondary alkyl bromides, 1,3-dithiane, and ethyl chloroformate. They were reacted with BrF3 to form the corresponding alpha,alpha-difluoro esters in 65-75% yield. Reaction conditions are very mild (1-2 min, 0 degreesC). The two sulfur atoms of the dithiane are essential for the reaction.