3-fluoro-3-phenylpropanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-fluoro-3-phenylpropanoic acid
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: XAPWSUNAWAWGHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯基丙酸 在 9-芴酮 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以81%的产率得到3-fluoro-3-phenylpropanoic acid
  参考文献：
  名称：

  可见光促进的无金属 C–H 活化：二芳基酮催化的选择性苄基单氟化和二氟化

  摘要：

  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。

  DOI：

  10.1021/ja410815u

文献信息

• [EN] GUANIDINE DERIVATIVES AS TRPC MODULATORS<br/>[FR] UTILISATION DE DÉRIVÉS DE LA GUANIDINE COMME MODULATEURS DES CANAUX TRPC
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2014016766A1

  公开（公告）日：2014-01-30

  The present invention is directed to guanidine derivatives as inhibitors of transient receptor potential canonical channels (TRPC channels), in particular TRPC3 and/or TRPC6 and/or TRPC7 activity, more particularly TRPC6 activity. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by TRPC channels (Formula (I)).

  本发明涉及胍啶衍生物作为瞬时受体电位经典通道（TRPC通道）的抑制剂，特别是TRPC3和/或TRPC6和/或TRPC7活性，更具体地是TRPC6活性。本文还提供了制备所述化合物的方法、用于合成的中间体、其药物组合物，以及治疗或预防由TRPC通道介导的疾病、症状和/或紊乱的方法（公式（I））。
• Metal-Catalyzed Benzylic Fluorination as a Synthetic Equivalent to 1,4-Conjugate Addition of Fluoride
  作者：Steven Bloom、Seth Andrew Sharber、Maxwell Gargiulo Holl、James Levi Knippel、Thomas Lectka

  DOI：10.1021/jo401796g

  日期：2013.11.1

  We explore in detail the iron-catalyzed benzylic fluorination of substrates containing aromatic rings and electron-withdrawing groups positioned β to one another, thus providing direct access to β-fluorinated adducts. This operationally convenient process can be thought of not only as a contribution to the timely problem of benzylic fluorination but also as a functional equivalent to a conjugate addition

  我们详细探讨了铁催化的含芳环和吸电子基团彼此位于β彼此之间的基团的苄基氟化，从而提供了直接接触β氟化加合物的途径。可以认为这种操作上便利的方法不仅有助于及时解决苄基氟化问题，而且还可以等同于与氟化物的共轭加成反应等价的功能，从而以中等至良好的收率和优异的选择性提供了产品。
• Photocatalyzed Benzylic Fluorination: Shedding “Light” on the Involvement of Electron Transfer
  作者：Steven Bloom、Michael McCann、Thomas Lectka

  DOI：10.1021/ol503094m

  日期：2014.12.19

  The photocatalyzed oxidation of benzylic compounds by 1,2,4,5-tetracyanobenzene (TCB) in the presence of Selectfluor provides a synthetically efficient route to electron deficient, less substituted, and otherwise inaccessible benzylic fluorides. The virtue of this system is multifold: it is metal-free and mild, and the reagents are inexpensive. Mechanistically, the data suggest the intimate formation of intermediate radical cations in the key radical forming step, as opposed to a concerted hydrogen atom transfer process.
• A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations
  作者：David Cantillo、Oscar de Frutos、Juan A. Rincón、Carlos Mateos、C. Oliver Kappe

  DOI：10.1021/jo5016757

  日期：2014.9.5

  A continuous-flow protocol for the light-induced fluorination of benzylic compounds is presented. The procedure uses Selectfluor as the fluorine source and xanthone as an inexpensive and commercially available photoorganocatalyst. The flow photoreactor is based on transparent fluorinated ethylene propylene tubing and a household compact fluorescent lamp. The combination of xanthone with black-light irradiation results in very efficient fluorination. Good to excellent isolated yields were obtained for a variety of substrates bearing different functional groups applying residence times below 30 min.
• PROPANOIC ACID DERIVATIVES AS INTEGRIN INHIBITORS
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP1133488A1

  公开（公告）日：2001-09-19