2-fluorocyclopentanone | 1755-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-fluorocyclopentanone
• 英文别名: 2-fluorocyclopentan-1-one
• CAS: 1755-12-0
• 化学式: C₅H₇FO
• 分子量: 102.108
• InChiKey: BHPDTMCXIHPYNM-UHFFFAOYSA-N

物化性质

• 沸点：
  57-59 °C(Press: 10 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-fluorocyclopentanone 在 甲醇 、 sodium tetrahydroborate 、 Novozyme 435 lipase 、 burkholderia cepacia lipase immobilized on diatomite 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 甲基叔丁基醚 为溶剂， 反应 18.0h， 生成 ((1R,2S)-2-fluorocyclopentyl)isoindolyl-1,3-dione
  参考文献：
  名称：

  Synthesis of optically active vicinal fluorocyclopentanols and fluorocyclopentanamines by enzymatic deracemization

  摘要：

  DOI：

  10.24820/ark.5550190.p011.634
• 作为产物：
  描述：

  1-acetoxycyclopentene 在 caesium fluoroxysulphate 作用下， 以 二氯甲烷 为溶剂， 生成 2-fluorocyclopentanone
  参考文献：
  名称：

  氟代硫酸铯在室温下氟化烯烃

  摘要：

  用氟代硫酸铯在室温下氟化1,1-二苯乙烯会形成2-氟-1,1-二苯乙烯; 降冰片-2-烯仅产生7-氟降三环烯和7-顺-氟降冰片-2-烯，而与各种环状烯醇乙酸酯的反应以高收率得到α-氟环烷酮。

  DOI：

  10.1039/c39810000795

文献信息

• Further studies on the synthesis of α-fluoro carbonyl compounds [1]
  作者：Gary L. Cantrell、Robert Filler

  DOI：10.1016/s0022-1139(00)80895-7

  日期：1985.1

  The trimethylsilyl enol ethers of cycloalkanones and acid esters are converted in high yields (70–90%) to the corresponding α-fluoro carbonyl derivative using XeF2 in CH2Cl2. Non-cyclic α-hydroxy ketones such as ethyl mandelate are efficiently transformed to the α-fluoro product by DAST and by Ishikawa's reagent. Nucleophilic displacement of halogen by fluoride failed in cyclic systems, giving instead

  在CH 2 Cl 2中使用XeF 2将环烷酮和酸酯的三甲基甲硅烷基烯醇醚以高收率（70-90％）转化为相应的α-氟代羰基衍生物。通过DAST和石川试剂将非环状α-羟基酮（如扁桃酸乙酯）有效地转化为α-氟产物。在循环系统中，氟化物对卤素的亲核取代作用失败，取而代之的是DMF或CH 3 CN（18-crown-6）中的α，β-不饱和酮和DMSO中的1,2-二酮，而KF为碱。DMSO氧化I（Br）F加合物的尝试未能产生α-氟代酮，但导致了脱氢卤化为-乙烯基氟。
• Chemistry of organo halogenic molecules. Part 100. Comparative behaviour of xenon diflouride and caesium fluoroxysulphate in the fluorination of enol acetates and ketones
  作者：Stojan Stavber、Boris Šket、Barbara Zajc、Marko Zupan

  DOI：10.1016/s0040-4020(01)89127-4

  日期：1989.1

  Xenon difluoride and caesium fluoroxysulphate reacted in methylene chloride or acetonitrile with various enol acetates, diketones, and ketones, yielding mainly α-fluoro ketones, the course of the reaction depending on the reagent and the structure of the organic molecule. Enol acetates from cycloakanones were converted with caesium fluoroxysulphate to α-fluorocycloalkanones in high yield. Xenon difluoride

  二氟化氙和氟代硫酸铯在二氯甲烷或乙腈中与各种烯醇乙酸酯，二酮和酮反应，主要生成α-氟代酮，反应过程取决于试剂和有机分子的结构。用氟代硫酸铯将来自环akanones的烯醇乙酸酯高产率地转化为α-氟代环烷酮。二氟化氙和氟代硫酸铯将苯并环烷酮-1的烯醇乙酸酯转化为α-氟苯并环烷酮，而苯并环烷酮-2的烯醇乙酸酯的反应性取决于所使用的试剂。用XeF 2和CsSO 4转化1,3-二苯基丙烷-1,3-二酮及其烯醇乙酸酯F为单和二氟取代的产物，反应过程取决于试剂。氟化二氙将1-茚满酮转化为重排的2，2-二氟苯并烷，而氟代硫酸铯与2-茚满酮反应生成1-氟-2-茚满酮。
• 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。
• Cantacuzene,J.; Ricard,D., Bulletin de la Societe Chimique de France, 1967, p. 1587 - 1593
  作者：Cantacuzene,J.、Ricard,D.

  DOI：——

  日期：——
• Reaction of Silyl Enol Ethers with Xenon Difluoride in MeCN:  Evidence for a Nonclassical Radical Cation Intermediate
  作者：Christopher A. Ramsden、Rachel G. Smith

  DOI：10.1021/ol990231e

  日期：1999.11.1

  The reactions of xenon difluoride in MeCN solution in Pyrex flasks with a series of TMS enol ethers have been investigated. The types of products formed are dependent on the structures of individual enol ethers, but under these conditions all products are consistent with a mechanism involving single electron transfer to un-ionized XeF2 giving a radical cation and subsequent formation of an alpha-fluoroketone, together with some ketone formation, The results suggest that if the radical cation is particularly stable, fluorodesilylation leads to radical formation, and solvent-derived products are then observed, Using other solvents, such as CFCl3 and C6F6, much more complex mixtures of products are obtained, and this is attributed to a different mode of reaction of xenon difluoride involving ionization to FXe+.