ethyl 2,2-difluoro-7-oxooctanoate | 134682-42-1

• 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-difluoro-7-oxooctanoate
• 英文别名: 2,2-Difluoro-7-oxo-octanoic acid ethyl ester
• CAS: 134682-42-1
• 化学式: C₁₀H₁₆F₂O₃
• 分子量: 222.232
• InChiKey: BXNVBQCZPYEGDM-UHFFFAOYSA-N

物化性质

• 沸点：
  272.9±40.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-chlorobutyl)-2-methyl[1,3]dioxolane 在 盐酸 、 正丁基锂 、 三氟化溴 作用下， 以 一氟三氯甲烷 为溶剂， 生成 ethyl 2,2-difluoro-7-oxooctanoate
  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

• 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.
• A new approach to .alpha.,.alpha.-difluoro-functionalized esters
  作者：Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00017a026

  日期：1991.8

  The addition reaction of iododifluoroacetates to alkenes is initiated by copper powder (10-20 mol %) at 50-60-degrees-C. Both terminal and internal alkenes give good yields of adducts. The reaction is also applicable to alkenes containing a variety of functional groups, such as epoxy, hydroxy, ketone, ester, and phosphonate moieties. This reaction can be carried out either neat or in solvents such as hexane, benzene, acetonitrile, DMF, DMSO, and HMPA and is suppressed by p-dinitrobenzene and di-tert-butyl nitroxide. A single electron transfer initiated radical mechanism is proposed. In the presence of nickel dichloride hexahydrate, reduction of the adducts with zinc in moist THF provides the corresponding alpha,alpha-difluoro esters in good yields.
• C–F Activation of Fluorinated Esters Using Photocatalytically Generated Diaminoalkyl Radical
  作者：Vladislav S. Kostromitin、Artem O. Sorokin、Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1021/acs.orglett.3c02570

  日期：2023.9.8
• 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.