4-氟-5-壬酮 | 101327-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氟-5-壬酮
• 英文名称: 4-Fluoro-5-nonanone
• 英文别名: 4-fluorononan-5-one
• CAS: 101327-89-3
• 化学式: C₉H₁₇FO
• 分子量: 160.232
• InChiKey: HVFXMDJVVWOWSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氟-5-壬酮 在 锂硼氢 作用下， 以 乙醚 为溶剂， 生成 syn-4-fluoro-5-nonanol 、 anti-4-fluoro-5-nonanol
  参考文献：
  名称：

  Chelation-Controlled Diastereoselective Reduction of α-Fluoroketones

  摘要：

  The effect of Ti-based Lewis acids on the reduction of alpha-fluoropropiophenone was examined to determine whether chelation control could be used to direct the diastereoselectivity of conversion to an alpha-fluoro alcohol. Pretreatment of alpha-fluoropropiophenone with TiCl4 followed by reduction with LiBH4 in diethyl ether or methylene chloride provided the syn diastereomer predominantly, while use of Ti(OiPr)4 under identical conditions provided the anti diastereomer as the major product. The products are consistent with a chelation-controlled mechanistic pathway in the former reduction and a nonchelation pathway in the latter case. Detailed 1H, 13C, and 19F NMR studies were consistent with chelation between TiCl4 and alpha-fluoropropiophenone under the reaction conditions utilized in this study. Reduction of other alpha-fluoroketones in the presence of TiCl4 also provided a high degree of diastereoselectivity in the conversion to alpha-fluoro alcohols, showing the generality of this approach.

  DOI：

  10.1021/ja052546x
• 作为产物：
  描述：

  5-壬酮 在 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以81%的产率得到4-氟-5-壬酮
  参考文献：
  名称：

  使用Accufluor TM -NFTh氟化试剂可高产率地对酮进行直接氟官能化

  摘要：

  使用1-氟-4-羟基-1,4-二氮杂双环[2,2,2]辛烷双（四氟硼酸酯）[Accufluor TM -NFTh]在乙腈溶液中。

  DOI：

  10.1016/0040-4039(96)00630-2

文献信息

• Micellar-System-Mediated Direct Fluorination of Ketones in Water
  作者：Stojan Stavber、Gaj Stavber、Marko Zupan

  DOI：10.1055/s-0028-1087924

  日期：2009.3

  A micellar system was developed and applied for direct regioselective fluorination of a variety of cyclic and acyclic ketones to α-fluoroketones in water as reaction medium with Selectfluor F-TEDA-BF 4 as fluorinating reagent. The inexpensive ionic amphiphile sodium dodecyl sulfate (SDS) was found to be an excellent promoter for fluorofunctionalization of hydrophobic ketones without prior activation

  以Selectfluor F-TEDA-BF 4 为氟化剂，开发了一种胶束体系，并应用于在水中将各种环状和无环酮直接区域选择性氟化成α-氟代酮作为反应介质。发现廉价的离子两亲物十二烷基硫酸钠 (SDS) 是疏水酮氟官能化的极好促进剂，无需事先活化或使用酸催化剂。
• High yield direct fluorofunctionalisation of ketones using AccufluorTM-NFTh fluorinating reagent
  作者：Stojan Stavber、Marko Zupan

  DOI：10.1016/0040-4039(96)00630-2

  日期：1996.5

  Direct regioselective conversion of a variety of cyclic and acyclic ketones to α-fluoroketones was achieved in high to excellent yield using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) [AccufluorTM - NFTh] in acetonitrile solution.

  使用1-氟-4-羟基-1,4-二氮杂双环[2,2,2]辛烷双（四氟硼酸酯）[Accufluor TM -NFTh]在乙腈溶液中。
• Preparation of .alpha.-fluoroketones
  申请人：F2 Chemicals Limited

  公开号：US06031139A1

  公开（公告）日：2000-02-29

  The use of polar organic solvent as the solvent in the direct fluorination, to make an .alpha.-fluoroketone, of an enol ester or enol trialkylsilyl ether of a compound containing a tautomerisable ketone group, the solvent being relatively inert to fluorine and one in which the enol ester or enol trialkylsilyl ether is relatively stable to hydrolysis. Preferably the solvent is anhydrous, e.g. anhydrous acetonitrile. Alternatively commercial formic acid containing 3% water may be used with a said enol ester.

  在直接氟化反应中，使用极性有机溶剂作为溶剂，以制备含有可互变异构酮基团的化合物的烯醇酯或烯醇三烷基硅醚的α-氟酮，所述溶剂对氟相对惰性，并且其中烯醇酯或烯醇三烷基硅醚对水解相对稳定。最好的情况是溶剂是无水的，例如无水乙腈。另外，也可以使用含有3%水的商业甲酸与所述烯醇酯一起使用。
• Synthesis of .alpha.-fluorocarbonyl compounds
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04215044A1

  公开（公告）日：1980-07-29

  Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms; each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms; R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms; R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.C group is carbocyclic, heterocyclic or haloheterocyclic, and recovering from the reaction mixture the compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3.

  制备化合物R.sup.2 R.sup.2 CFC(O)R.sup.3的过程，包括在惰性溶剂的反应混合物中，将ROF和##STR1##在-40℃至-100℃的温度下接触并反应；其中R为1-6个碳原子的多氟-多卤代烷基或FOCF.sub.2；R.sup.1为1-6个碳原子的烃基；每个R.sup.2从H、1-17个碳原子的烷基、3-6个碳原子的环烷基、芳基、杂芳基以及这样的烷基、环烷基、芳基和杂芳基被卤素或1-6个碳原子的烷氧基取代中选择；R.sup.3从H、1-16个碳原子的烷基和卤代烷基、3-10个碳原子的环烷基、芳基和卤代芳基、OSi(R.sup.1).sub.3、OH、NH.sub.2、1-6个碳原子的烷氧基、芳氧基、NHR.sup.1和NR.sup.1.sub.2中选择，其中R.sup.1为1-6个碳原子的烷基、N-芳基氨基和4-5个碳原子的氮或硫杂环；R.sup.3和一个R.sup.2组成的二元基与C.dbd.C基团一起是碳环、杂环或卤杂环，从反应混合物中回收化合物R.sup.2 R.sup.2 CFC(O)R.sup.3。
• Direct Electrophilic α-Fluorination of Imines:  Efficient Synthesis of Mono- and Difluoroimines
  作者：Guido Verniest、Eva Van Hende、Riccardo Surmont、Norbert De Kimpe

  DOI：10.1021/ol061720z

  日期：2006.10.1

  A mild and efficient procedure to synthesize alpha-fluoro- and alpha,alpha-difluoroimines was developed. Various N-alkylimines derived from acetophenones were successfully monofluorinated using NFSI (N-fluorobenzenesulfonimide) in a mixture of CH3CN and DMF at 0 degrees C. Alternatively, the same procedure without DMF gave rise to difluorinated imines when performed at room temperature. The obtained alpha- and alpha,alpha-difluorinated imines were subsequently reduced to give the corresponding beta-fluoro- and beta,beta-difluoroamines in good yield.