(E)-3-fluoro-1-phenylbut-2-en-1-one | 1198158-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-fluoro-1-phenylbut-2-en-1-one
• 英文别名: 3-fluoro-1-phenyl-2-buten-1-one
• CAS: 1198158-20-1
• 化学式: C₁₀H₉FO
• 分子量: 164.179
• InChiKey: AFNRWGZBZKNNAY-BQYQJAHWSA-N

物化性质

• 沸点：
  215.6±36.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (E)-3-fluoro-1-phenylbut-2-en-1-one 在 钾硼氢 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以78%的产率得到苄叉丙酮
  参考文献：
  名称：

  Synthesis of β-fluoroenones and their reductive rearrangement in aqueous media

  摘要：

  In this paper, a simple and efficient preparation of beta-fluoroenones, as a mixture of E/Z isomers with the E-isomer as the main product, from 1,2-allenic ketones by using TBAF center dot 3H(2)O in water as a nucleophilic fluorination agent has been developed. Moreover, in exploring the synthetic applications of b-fluoroenones, an unprecedented reductive defluorination rearrangement of beta-fluoroenones toward enones under mild conditions in aqueous media was also discovered. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.065
• 作为产物：
  描述：

  1-phenylbuta-2,3-dien-1-one 在 四丁基氟化铵 作用下， 以 水 为溶剂， 反应 0.33h， 以58%的产率得到(E)-3-fluoro-1-phenylbut-2-en-1-one
  参考文献：
  名称：

  Synthesis of β-fluoroenones and their reductive rearrangement in aqueous media

  摘要：

  In this paper, a simple and efficient preparation of beta-fluoroenones, as a mixture of E/Z isomers with the E-isomer as the main product, from 1,2-allenic ketones by using TBAF center dot 3H(2)O in water as a nucleophilic fluorination agent has been developed. Moreover, in exploring the synthetic applications of b-fluoroenones, an unprecedented reductive defluorination rearrangement of beta-fluoroenones toward enones under mild conditions in aqueous media was also discovered. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.065

文献信息

• Regioselective synthesis of β-fluoro-α,β-unsaturated ketones by the reaction of β-diketones with DFMBA
  作者：Keisuke Sano、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1016/j.jfluchem.2009.05.009

  日期：2009.8

  The deoxyfluorination reaction of beta-diketones with N,N-diethyl-alpha,alpha-difluoro-m-methylbenzylamine (DFMBA) gave beta-fluoro-alpha,beta-unsaturated ketones in good yields. The reaction proceeded regioselectively, and only one regioisomer was obtained from the unsymmetrical 1-aryl-1,3-diketones. The reaction is applicable to diketones with a trifluoromethyl group, obtaining good yields of 3,4,4,4-tetrafluorobutenones. We used the resulting beta-fluoro-alpha,beta-unsaturated ketones for the reaction with lithium dialkyl cuprates. (C) 2009 Elsevier B.V. All rights reserved.
• Synthesis of β-fluoroenones and their reductive rearrangement in aqueous media
  作者：Yan He、Nana Shen、Xuesen Fan、Xinying Zhang

  DOI：10.1016/j.tet.2013.07.065

  日期：2013.10

  In this paper, a simple and efficient preparation of beta-fluoroenones, as a mixture of E/Z isomers with the E-isomer as the main product, from 1,2-allenic ketones by using TBAF center dot 3H(2)O in water as a nucleophilic fluorination agent has been developed. Moreover, in exploring the synthetic applications of b-fluoroenones, an unprecedented reductive defluorination rearrangement of beta-fluoroenones toward enones under mild conditions in aqueous media was also discovered. (C) 2013 Elsevier Ltd. All rights reserved.