(R)-α-fluoro-α-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: (R)-α-fluoro-α-phenylpropionic acid
• 英文别名: (R)-(-)-l'acide 2-fluoro-2-phenyl propanoique；(R)-(-)-2-fluoro-2-phenylpropanoic acid；(R)-2-Fluoro-2-phenylpropionic acid；(R)-2-fluoro-2-phenylpropanoic acid；(S)-2-fluoro-2-phenylpropionic acid；(2R)-2-Fluoro-2-phenylpropanoic acid
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: UQZSHNJGBJJFJN-SECBINFHSA-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

• 作为产物：
  描述：

  2-苯基丙酸 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 过氧化氢苯甲酰 、 chlorure de thionyle 、 四丁基溴化铵 、 氟化氢吡啶 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 134.0h， 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

文献信息

• A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids
  作者：Atsushi Tengeiji、Isamu Shiina

  DOI：10.3390/molecules17067356

  日期：——

  We report a new method for the preparation of chiral 2-aryl-2-fluoropropanoic acids, including 2-fluoroibuprofen, a fluorinated analogue of non-steroidal anti-inflammatory drugs (NSAIDs), by the kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids using enantioselective esterification. By applying pivalic anhydride (Piv2O) as a coupling agent, bis(α-naphthyl)methanol [(α-Np)2CHOH] as an achiral

  我们报告了一种制备手性 2-芳基-2-氟丙酸的新方法，包括 2-氟布洛芬，一种非甾体抗炎药 (NSAID) 的氟化类似物，通过外消旋 2-芳基-2 的动力学分辨率-氟丙酸使用对映选择性酯化。通过应用新戊酸酐 (Piv2O) 作为偶联剂，双 (α-萘基) 甲醇 [(α-Np)2CHOH] 作为非手性醇，和 (+)-苯并四甲醚 (BTM) 作为手性酰基转移催化剂，一系列外消旋 2-芳基-2-氟丙酸被动力学分离，以提供光学活性羧酸和相应的酯，具有良好到高度的对映体过量。
• Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells
  作者：Yoshimitsu Yamazaki、Shiro Yusa、Yu-ichi Kageyama、Hirohito Tsue、Ken-ichi Hirao、Hiroaki Okuno

  DOI：10.1016/s0022-1139(96)03485-9

  日期：1996.8

  towards (S) -2b by other cells such as ras oncogenetransformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated ( ±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making estertype anticancer prodrugs more specific to cancer cells.

  （±）2-氟-2-苯基乙酸乙酯被几种大鼠癌细胞系的培养细胞立体选择性地水解，得到富含R对映异构体的羧酸。立体选择性增加了（±）-2-氟-2-苯基（2B与所有本细胞系）和（±）-2-苯基-3,3,3-三氟代（3b）的与大鼠肝癌McA- RH7777细胞系。立体选择性对于不同的细胞系是不同的，因为McA-RH7777细胞更偏爱（R）-2b，而其他细胞（如ras）偏爱（S）-2b癌基因转化的大鼠肝脏Anr4细胞。这些立体选择性不同于未氟化的（±）-2-苯基丙酸乙酯。因此，氟原子被癌细胞的酯水解酶识别，并且酰基上的氟取代将用于使酯型抗癌前药对癌细胞更具特异性。
• A versatile approach to optically active primary 2-fluoro-2-phenylalkanols through lipase-catalyzed transformations
  作者：Olav Goj、Annegret Burchardt、Günter Haufe

  DOI：10.1016/s0957-4166(96)00501-0

  日期：1997.2

  resolutions of (±)-1-acetoxy-2-fluoro-2-phenylalkanes 1 by enzymatic hydrolysis and of (±)-2-fluoro-2-phenylpropanol 2a by lipase-catalyzed acetylation are described for the first time. Hydrolysis of (±)-1 with lipase Amano PS (Pseudomonas cepacia) provided both the optically active acetates (−)-1 and the corresponding primary alcohols (−)-2 with high enantiomeric excess. (R)-enantiopreference was

  首次描述了通过酶促水解的（±）-1-乙酰氧基-2-氟-2-苯基链烷烃1和通过脂肪酶催化的乙酰化的（±）-2-氟-2-苯基丙醇2a的动力学拆分。用脂肪酶Amano PS （Pseudomonas cepacia）水解（±）-1可提供旋光性乙酸酯（-）- 1和相应的伯醇（-）- 2，其对映体过量较高。与未氟化的母体化合物（±）-2-苯基丙醇3相比，（R）-对映体优选的是（±）-2-氟-2-苯基丙醇2a的乙酰化，其对映选择性和转化率更高。
• Novel Quinazoline Derivatives and Their Medical Use
  申请人：Brown William Dalby

  公开号：US20090291973A1

  公开（公告）日：2009-11-26

  This invention relates to novel quinazoline derivatives having medical utility, to use of the quinazoline derivatives of the invention for the manufacture of a medicament, to pharmaceutical compositions comprising the quinazoline derivatives of the invention, and to methods of treating a disorder, disease or a condition of a subject, which disorder, disease or condition is responsive to activation of K v 7 channels.

  本发明涉及具有医学用途的新型喹唑啉衍生物，涉及使用本发明的喹唑啉衍生物制造药物，涉及含有本发明的喹唑啉衍生物的药物组合物，以及涉及治疗响应于Kv7通道激活的主体的紊乱、疾病或状况的方法。
• Acide 2-fluoro-2-phényl propanoïque: préparation et utilisation comme agent chiral de dérivation
  作者：S. Hamman

  DOI：10.1016/s0022-1139(00)80036-6

  日期：1993.2

  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.