2-氟己酸 | 1578-57-0

• 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: 2-氟己酸
• 英文名称: 2-fluorohexanoic acid
• 英文别名: 2-Fluor-hexansaeure
• CAS: 1578-57-0
• 化学式: C₆H₁₁FO₂
• 分子量: 134.151
• InChiKey: CDWPBSAPAJJTHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟己酸 在 盐酸 、 正丁基锂 、 磺酰氯 、 二异丙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 15.5h， 生成 (S)-2-fluoro-2-methylhexanoic acid
  参考文献：
  名称：

  Directed resolution of 2-fluoro-2-methylhexanoic acid

  摘要：

  DOI：

  10.1016/s0022-1139(00)81934-x
• 作为产物：
  描述：

  1-Methoxy-1-(phenylthio)-2-fluoro-1-hexene 在 硫酸 作用下， 反应 5.0h， 以95%的产率得到2-氟己酸
  参考文献：
  名称：

  Electrolytic reactions of fluoro organic compounds. 7. Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides. Preparation of highly useful trifluoromethylated building blocks

  摘要：

  Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides and the corresponding nonfluorinated sulfides were comparatively studied. It was found that a trifluoromethyl group remarkably promoted anodic substitution and methoxy and acetoxy groups were introduced adjacent to the trifluoromethyl group of the sulfides. Longer perfluoroalkyl groups also promoted these anodic substitutions. These products were shown to be highly useful building blocks for the synthesis of fluoro organic compounds.

  DOI：

  10.1021/jo00001a028

文献信息

• THE SYNTHESIS OF α-MONOFLUOROALKANOIC ACIDS
  作者：F. L. M. Pattison、R. L. Buchanan、F. H. Dean

  DOI：10.1139/v65-224

  日期：1965.6.1

  α-Monofluoroalkanoic acids are important intermediates in the synthesis of biologically active fluorine compounds. General methods of preparation have been examined, based on the three following reagents: (a) hydrogen fluoride + N-bromoacetamide; (b) diethyl monofluoromalonate; and (c) perchloryl fluoride. The first of these is the recommended procedure for simple unsubstituted α-fluoro acids; however, the

  α-单氟链烷酸是合成生物活性氟化合物的重要中间体。已根据以下三种试剂检查了一般制备方法： (a) 氟化氢 + N-溴乙酰胺；(b) 单氟丙二酸二乙酯；(c) 全氯酰氟。其中第一个是简单的未取代 α-氟酸的推荐程序；然而，氟丙二酸路线不太活跃，因此是那些含有不稳定官能团的 α-氟代酸的首选方法。
• Absolute Rate Constants for Radical Additions to Alkenes in Solution. The Synergistic Effect of Perfluorination on the Reactivities of <i>n</i>-Alkyl Radicals¹
  作者：David V. Avila、K. U. Ingold、J. Lusztyk、W. R. Dolbier、H.-Q. Pan

  DOI：10.1021/jo951782v

  日期：1996.1.1

  determine the absolute rate constants for addition of several partially fluorinated n-alkyl radicals to three styrenes at 25 °C in Freon 113. Fluorination at the γ-position (RCF2CH2CH2•) gives radicals with essentially the same reactivity as non-fluorinated n-alkyls. The RCH2CF2CH2• and RCH2CH2CHF• radicals are both about three times as reactive as RCF2CH2CH2•, but the RCH2CH2CF2• radical is ca. five to six

  在25°C的氟利昂113中，已经使用激光闪光光解法确定了将几个部分氟化的n-烷基自由基加到三个苯乙烯中的绝对速率常数。在γ位置的氟化（RCF2CH2CH2•）产生的自由基具有基本相同的反应性作为非氟化的正烷基。RCH2CF2CH2•和RCH2CH2CHF•自由基的活性均约为RCF2CH2CH2•的三倍，但RCH2CH2CF2•的自由基约为ca。五到六次而不是大约 是RCH2CH2CHF•的三倍。类似地，全氟自由基CF3CF2CF2•的反应性比基于RCH2CF2CH2•和RCH2CH2CF2•的反应性所预期的要高得多。因此，全氟化的正烷基比根据α-，β-和γ-氟化作用的单独作用所预测的反应性要高得多。
• Electrolytic transformation of functional groups of fluoroorganic compounds. I. Anodic methoxylation and acetoxylation of trifluoroethyl sulfide
  作者：Toshio Fuchigami、Yuuki Nakagawa、Tsutomu Nonaka

  DOI：10.1016/s0040-4039(00)83902-7

  日期：1986.1

  Anodic methoxylation and acetoxylation of phenyl trifluoroethyl sulfide were successfully performed to give the corresponding α-methoxy and α-acetoxy sulfides in good to excellent yields, respectively. These products were found to be useful building blocks for the synthesis of fluoroorganic compounds.

  成功进行了苯基三氟乙基硫醚的阳极甲氧基化和乙酰氧基化反应，分别以良好或优异的收率得到了相应的α-甲氧基和α-乙酰氧基硫化物。发现这些产物是合成氟有机化合物的有用组成部分。
• PREPARATION AND SYNTHETIC UTILITY OF DIFLUOROKETENE THIOACETAL. A NOVEL SYNTHETIC ROUTE TOα-MONOFLUOROALKANOIC ACIDS
  作者：Kiyoshi Tanaka、Takeshi Nakai、Nobuo Ishikawa

  DOI：10.1246/cl.1979.175

  日期：1979.2.5

  Difluoroketene thioacetal (2) prepared from trifluoroacetaldehyde thioacetal (3) with lithium diisopropylamide or alkyllithiums has been shown to be useful as a building block for the preparation of α-monofluoroalkanoic acids (5), which involves the reaction of 2 with various organometallic compounds followed by hydrolysis of the resulting monofluoroketene thioacetal (4).

  由三氟乙醛硫缩醛 (3) 与二异丙基氨基锂或烷基锂制备的二氟乙烯酮硫缩醛 (2) 已被证明可用作制备 α-单氟链烷酸 (5) 的结构单元，其中涉及 2 与各种有机金属化合物的反应，然后通过水解生成的单氟乙烯酮硫缩醛 (4)。
• Electrolysis of α-Chloro- and α-Fluorocarboxylic Acids
  作者：Parkash C. Arora、R. G. Woolford

  DOI：10.1139/v71-445

  日期：1971.8.15

  The electrolysis of α-chlorovaleric, α-chlorocaproic, and α-chloroisobutyric acids in methanol gave none of the Kolbe dimer; the main products were chloroester and hydrogen ester with aldehydes and acetals formed in lesser amounts. In water, straight chain α-chloroacids gave dimeric esters as the major product. However, Kolbe dimer was formed in fairly good yields together with small amounts of fluoroester and acetal, when α-fluorocaproic and α-fluoroheptanoic acids were electrolyzed in methanol. No Kolbe dimer was produced from 2-fluoro-2-ethylbutanoic and α-fluorophenylacetic acids; the corresponding ketone or aldehyde was the major product.

  在甲醇中电解α-氯戊酸、α-氯己酸和α-氯异丁酸，没有生成Kolbe二聚体；主要产物是氯酯和氢酯，少量生成醛和缩醛。在水中，直链α-氯酸产生二聚酯作为主要产物。然而，当α-氟己酸和α-氟庚酸在甲醇中电解时，Kolbe二聚体产率相当高，同时还有少量氟酯和缩醛。2-氟-2-乙基丁酸和α-氟苯乙酸没有产生Kolbe二聚体，相应的酮或醛是主要产物。