3-fluoro-2-octanone | 178484-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-fluoro-2-octanone
• 英文别名: 3-fluoro-octan-2-one；3-Fluorooctan-2-one
• CAS: 178484-14-5
• 化学式: C₈H₁₅FO
• 分子量: 146.205
• InChiKey: QSYBKGCBEXOOJV-UHFFFAOYSA-N

物化性质

• 沸点：
  177.9±10.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3-fluoro-2-octanone 在 溴 作用下， 生成 4-bromo-4-fluoro-octan-2-one
  参考文献：
  名称：

  Kirrmann,A.; Nouri-Bimorghi,R., Bulletin de la Societe Chimique de France, 1972, p. 2328 - 2331

  摘要：

  DOI：
• 作为产物：
  描述：

  仲辛酮 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 10.0h， 以78%的产率得到3-fluoro-2-octanone
  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

• 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。
• Elemental fluorine. Part 19: Electrophilic fluorination of hexyl derivatives bearing electron withdrawing groups
  作者：Richard D. Chambers、Mandy Parsons、Graham Sandford、Emmanuelle Thomas、Jelena Trmcic、John S. Moilliet

  DOI：10.1016/j.tet.2006.03.113

  日期：2006.7

  Reaction of a series of model hexyl derivatives of the form C6H13–X (X=Cl, Br, I, CO2Me, COMe, CHO) with both elemental fluorine and Selectfluor™ was studied in order to assess the impact of electron withdrawing functional groups upon fluorination of an alkyl chain. Fluorination generally occurs at secondary sites, with a slight preference for those that are furthest removed from the electron withdrawing

  研究了一系列形式为C 6 H 13 –X（X = Cl，Br，I，CO 2 Me，COMe，CHO）的模型己基衍生物与元素氟和Selectfluor™的反应，以评估氟的影响。烷基链氟化时的吸电子官能团。氟化通常发生在次要位置，与亲电子取代过程一致，略微偏爱从吸电子基团离得最远的位置，尽管在大多数情况下会获得氟化产物的混合物。
• Chelation-Controlled Diastereoselective Reduction of α-Fluoroketones
  作者：Pramod K. Mohanta、Todd A. Davis、Jeremy R. Gooch、Robert A. Flowers

  DOI：10.1021/ja052546x

  日期：2005.8.1

  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.
• 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。
• Kirrmann,A.; Nouri-Bimorghi,R., Bulletin de la Societe Chimique de France, 1972, p. 2328 - 2331
  作者：Kirrmann,A.、Nouri-Bimorghi,R.

  DOI：——

  日期：——