isopropyl 2,2-difluoro-12-hydroxydodecanoate | 140420-97-9

• 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-12-hydroxydodecanoate
• 英文别名: Propan-2-yl 2,2-difluoro-12-hydroxydodecanoate
• CAS: 140420-97-9
• 化学式: C₁₅H₂₈F₂O₃
• 分子量: 294.382
• InChiKey: UMRSNUGTCGPMBI-UHFFFAOYSA-N

物化性质

• 沸点：
  346.3±27.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-十烯-1-醇 、 isopropyl iododifluoroacetate 在 水 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到isopropyl 2,2-difluoro-12-hydroxydodecanoate
  参考文献：
  名称：

  A novel and practical method for the preparation of α,α-difluoro functionalized esters

  摘要：

  α,α-二氟官能化酯可以通过在二氯化镍六水合物催化量的存在下，由碘二氟乙酸酯与烯烃和锌反应，以良好的收率制备得到。

  DOI：

  10.1039/c39920000233

文献信息

• 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
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00045a027

  日期：1992.9

  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.