isopropyl 2,2-difluoro-6-methyl-6-carbethoxyhexanoate | 143105-14-0

• 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: isopropyl 2,2-difluoro-6-methyl-6-carbethoxyhexanoate
• 英文别名: 7-O-ethyl 1-O-propan-2-yl 2,2-difluoro-6-methylheptanedioate
• CAS: 143105-14-0
• 化学式: C₁₃H₂₂F₂O₄
• 分子量: 280.312
• InChiKey: RMOZDDDDRYHXDA-UHFFFAOYSA-N

物化性质

• 沸点：
  290.3±40.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲基-4-戊烯酸乙酯 、 isopropyl iododifluoroacetate 在 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到isopropyl 2,2-difluoro-6-methyl-6-carbethoxyhexanoate
  参考文献：
  名称：

  Nickel-catalyzed reaction of iododifluoroacetates with alkenes and zinc: a novel and practical route to .alpha.,.alpha.-difluoro-functionalized esters and .alpha.,.alpha.,.omega.,.omega.-tetrafluoro diesters

  摘要：

  lododifluoroacetates 1a-c react with alkenes and zinc in the presence of nickel dichloride hexahydrate in THF at room temperature or 60-degrees-C to give the corresponding alpha,alpha-difluoro esters in good yields. The reaction is also applicable to alkenes containing a variety of functional groups such as trimethylsilyl, hydroxy, ketone, and ester moieties. The reaction of 1 works well with dienes; the products formed depend on the length of chain of the dienes. 1,8-Nonadiene and 1,5-hexadiene afford the alpha,alpha,omega,omega-tetrafluoro diesters, while 1,6-heptadiene gave a mixture of ethyl 2,2-difluoro-8-nonenoate (19) and the cyclopentyl-substituted alpha,alpha-difluoro ester 20. When diallyl ether was used as a substrate, only the tetrahydrofuran derivative 21 was formed. The nickel-catalyzed reaction can be suppressed by p-dinitrobenzene and hydroquinone. A single electron transfer initiated radical mechanism is proposed.

  DOI：

  10.1021/jo00045a027