methyl 3-fluoro-3-phenylpropanoate | 188941-05-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-fluoro-3-phenylpropanoate
• 英文别名: Methyl 3-fluoro-3-phenylpropanoate
• CAS: 188941-05-1
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: YCBBIQUHEIMEJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯丙酸甲酯 在 tetrakis(tetrabutylammonium)decatungstate(VI) 、 碳酸氢钠 、 N-氟代双苯磺酰胺 作用下， 以 乙腈 为溶剂， 以62%的产率得到methyl 3-fluoro-3-phenylpropanoate
  参考文献：
  名称：

  N-氟苯磺酰亚胺对苄基CH键的直接光催化氟化

  摘要：

  描述了使用AIBN引发或分解钨酸盐的光催化作用，用NFSI直接将苄基CH键氟化的两种互补策略。

  DOI：

  10.1039/c5cc04058b

文献信息

• Visible Light-Promoted Metal-Free C–H Activation: Diarylketone-Catalyzed Selective Benzylic Mono- and Difluorination
  作者：Ji-Bao Xia、Chen Zhu、Chuo Chen

  DOI：10.1021/ja410815u

  日期：2013.11.20

  the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while

  我们在此报告了一种将苄基 CH 基团直接转化为 CF 的操作简单的方法。我们表明可见光可以激活二芳基酮以选择性地提取苄基氢原子。添加氟自由基供体产生苄基氟并再生催化剂。单氟化和二氟化产物的选择性形成可以通过催化剂控制来实现。9-芴酮催化苄基CH单氟化，而呫吨酮催化苄基CH二氟化。这种新的 CH 氟化方法的范围和效率明显优于现有方法。这也是选择性CH gem-二氟化的第一份报告。
• Direct photocatalytic fluorination of benzylic C–H bonds with N-fluorobenzenesulfonimide
  作者：Matthew B. Nodwell、Abhimanyu Bagai、Shira D. Halperin、Rainer E. Martin、Henner Knust、Robert Britton

  DOI：10.1039/c5cc04058b

  日期：——

  Two complimentary strategies for the direct fluorination of benzylic C-H bonds with NFSI are described using either AIBN-initiation or decatungstate photocatalysis.

  描述了使用AIBN引发或分解钨酸盐的光催化作用，用NFSI直接将苄基CH键氟化的两种互补策略。
• Iron(II)-Catalyzed Benzylic Fluorination
  作者：Steven Bloom、Cody Ross Pitts、Ryan Woltornist、Andrew Griswold、Maxwell Gargiulo Holl、Thomas Lectka

  DOI：10.1021/ol400424s

  日期：2013.4.5

  Direct C-F functionalization of benzylic sp(3) C-H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to beta-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to alpha,beta-unsaturated ketones.
• Triethylborane-Initiated Radical Chain Fluorination: A Synthetic Method Derived from Mechanistic Insight
  作者：Cody Ross Pitts、Bill Ling、Ryan Woltornist、Ran Liu、Thomas Lectka

  DOI：10.1021/jo501520e

  日期：2014.9.19

  We offer a mild, metal-free sp(3) C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane--an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.
• Exploring the Reducing Ability of Organic Dye (Acr⁺-Mes) for Fluorination and Oxidation of Benzylic C(sp³)–H Bonds under Visible Light Irradiation
  作者：Ming Xiang、Zhi-Kun Xin、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.7b01270

  日期：2017.6.2

  The excellent oxidizing capability of acridinium-based organic dye (Acr(+)-Mes) is fully studied in photoredox catalysis. However, its reducing ability is always considered weak for organic transformation. The reducing ability of Acr(+)-Mes is developed by Selectfluor to achieve effective fluorination and oxidation of benzylic C(sp(3))-H bonds under visible light irradiation, which is not available for the direct use of oxidizing ability of excited Acr(+)-Mes. Mechanistic insights provided strong evidence for the oxidative quenching of Acr(+)-Mes.