(+/-)-2-Fluoro-2-phenylpropionic acid

• 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: (+/-)-2-Fluoro-2-phenylpropionic acid
• 英文别名: Phenylmethylfluoressigsaeure；2-fluoro-2-phenylpropanoic acid
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: UQZSHNJGBJJFJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-Fluoro-2-phenylpropionic acid 生成 (R)-α-fluoro-α-phenylpropionic acid
  参考文献：
  名称：

  Acide 2-fluoro-2-phényl propanoïque: préparation et utilisation comme agent chiral de dérivation

  摘要：

  The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is [alpha]20D, =-28.5-degrees (c=1.5, ethanol). This acid has been used as a chiral derivatizing agent. Esters and amides prepared from this acid and chiral alcohols or amines present important fluorine chemical shift differences between the diastereoisomers.

  DOI：

  10.1016/s0022-1139(00)80036-6
• 作为产物：
  描述：

  2-苯基丙酸 在 Selectfluor 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (+/-)-2-Fluoro-2-phenylpropionic acid
  参考文献：
  名称：

  一种制备α-氟-α-芳基羧酸的新颖的通用方法。与硅烷的Selectfluor烯酮缩醛直接氟化®

  摘要：

  用TBSCl和加入LiHMDS在THF中的α-芳基羧酸的反应得到双甲硅烷基乙烯酮缩二醇，将其直接用廉价的Selectfluor氟化®以产生高收率的相应的α氟-α-芳基羧酸。还描述了该方法在从相应的羧酸酯合成α-氟代羧酸酯中的应用。

  DOI：

  10.1016/j.tetlet.2006.08.057

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））。
• A novel general method for preparation of α-fluoro-α-arylcarboxylic acid. Direct fluorination of silyl ketene acetals with Selectfluor®
  作者：Fei Zhang、Jake Z. Song

  DOI：10.1016/j.tetlet.2006.08.057

  日期：2006.10

  The reaction of an α-arylcarboxylic acid with TBSCl and LiHMDS in THF yielded bis-silyl ketene acetal, which was directly fluorinated with inexpensive Selectfluor® to produce the corresponding α-fluoro-α-arylcarboxylic acid in high yield. Application of the methodology to the synthesis of α-fluorocarboxylic ester from the corresponding carboxylic ester is also described.

  用TBSCl和加入LiHMDS在THF中的α-芳基羧酸的反应得到双甲硅烷基乙烯酮缩二醇，将其直接用廉价的Selectfluor氟化®以产生高收率的相应的α氟-α-芳基羧酸。还描述了该方法在从相应的羧酸酯合成α-氟代羧酸酯中的应用。
• α-Fluoro analogues of inflammation inhibiting α-arylpropionic acids
  作者：Manfred Schlosser、Dominique Michel、Zhi-wei Guo、Charles J. Sih

  DOI：10.1016/0040-4020(96)00411-5

  日期：1996.6

  2-Aryl-2-fluoropropionic acids were prepared by treatment of either ethyl α-hydroxy-carboxylates or cyanohydrin O-silyl ethers with diethylaminosulfur trifluoride and subsequent hydrolysis. The methyl ester of 2-fluoro-2-(4-isobutylphenyl)propionic acid (“α-fluoroibuprofen”) was submitted to an enzymatic racemate resolution.

  通过用三氟化二乙基氨基硫处理α-羟基羧酸乙酯或氰醇O-甲硅烷基醚并随后水解来制备2-芳基-2-氟丙酸。使2-氟-2-（4-异丁基苯基）丙酸的甲酯（“α-氟布洛芬”）达到酶促外消旋体拆分。
• Electrochemical Carboxylation of α,α-Difluorotoluene Derivatives and Its Application to the Synthesis of α-Fluorinated Nonsteroidal Anti-Inflammatory Drugs
  作者：Hisanori Senboku、Yusuke Yamauchi、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1055/s-2008-1032069

  日期：2008.2

  Electrochemical carboxylation of α,α-difluorotoluene derivatives resulted in an efficient fixation of carbon dioxide to give the corresponding α-fluorophenylacetic acids in good yields, and this reaction was successfully applied to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs (NSAIDs).

  α,α-二氟甲苯衍生物的电化学羧化反应有效地固定了二氧化碳，生成了相应的α-氟苯乙酸，并且该反应成功应用于合成α-氟化非甾体抗炎药（NSAIDs）。
• Synthesis of 2-Fluoro- Acids, Esters, and Amides From Ã-Dicyanoepoxides
  作者：A. Ould Amanetoullah、M. M. Chaabouni、A. Baklouti

  DOI：10.1080/00397919608003723

  日期：1996.3

  Abstract The opening of A-dicyanoepoxides by pyridine polyhdrofluoride yields polymerisable 2-fluorocyanoformyls which may be kept intact when diluated in dichloromethane or ether. These intermediates react with nuclecophiles such as water, methanol or amines to give respectivly 2-fluoroacids, esters or amides.

  摘要 A-二氰基环氧化物被吡啶多氟化物打开，产生可聚合的 2-氟氰基甲酰基，在二氯甲烷或乙醚中稀释时可以保持完整。这些中间体与亲核试剂如水、甲醇或胺反应，分别得到 2-氟酸、酯或酰胺。