2-氟-2-(4-甲基苯基)乙腈 | 106468-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氟-2-(4-甲基苯基)乙腈
• 英文名称: 2-fluoro-2-(4-methylphenyl)ethanenitrile
• 英文别名: 2-Fluoro-2-(4-methylphenyl)acetonitrile
• CAS: 106468-03-5
• 化学式: C₉H₈FN
• 分子量: 149.168
• InChiKey: NXBMFRPCCALTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氟-2-(4-甲基苯基)乙腈 在 HCl buffer 、 nitrolase from Arabidopsis thaliana 、 三羟甲基氨基甲烷 作用下， 以 甲醇 、 水 为溶剂， 反应 9.5h， 以67%的产率得到2-fluoro-2-(4-methylphenyl)acetamide
  参考文献：
  名称：

  Enantioselective hydrolysis of (RS)-2-fluoroarylacetonitriles using nitrilase from Arabidopsis thaliana

  摘要：

  The enzymatic resolution of 2-fluoroarylacetonitriles (RS)-3 using nitrilase from the plant Arabidopsis thaliana is described. Racemic 2-fluoronitriles 3 are easily accessible from O-silylated aromatic cyanohydrins 2 by reaction with DAST. The nitriles (RS)-3 were hydrolysed with the nitrilase as a catalyst, not to the expected 2-fluoroarylacetic acids but to the corresponding (R)-2-fluoroarylacetamides (R)-5 as the main products. After optimization of reaction conditions (pH 9, 7 degreesC), the enantiomeric excesses of (R)-5a,c and f (R=H, 3-Me, 3-OMe) could be improved to >99% by one recrystallization. The acid catalysed hydrolysis of (R)-5a,5c and 5f afforded the corresponding (R)-2-fluoroarylacetic acids (R)-4a,Je and 4f without racemization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00034-9
• 作为产物：
  描述：

  对甲基苯乙腈 在 正丁基锂 、 Selectfluor 作用下， 以 四氢呋喃 为溶剂， 以35%的产率得到2-氟-2-(4-甲基苯基)乙腈
  参考文献：
  名称：

  Convenient fluorination of nitro and nitrile compounds with Selectfluor

  摘要：

  A variety of nitro and nitrile compounds were fluorinated in good yields by Selectfluor under mild conditions. For these transformations to be successful, it is crucial to select proper amounts of an appropriate base as a function of the properties of the substrate and also to use Selectfluor only as required. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.056

文献信息

• Etude de la regioselectivite en fluoration anodique de derives benzyliques
  作者：Eliane Laurent、Bernard Marquet、Robert Tardivel

  DOI：10.1016/s0040-4020(01)86437-1

  日期：1991.1

  By anodic oxidation of paramethylbenzylsulfonate, ester and nitrite in Et3N,3HF/CH3CN, regioselective functionalization at benzylic positions is obtained (benzylic fluorides and acetamides are formed). In order to examin the determining factors of the chemioselectivity. It was compared to those obtained in bromination of the same compounds by 1,3-dibromo 5,5-dimethylhydantoïn (DBH)/2.2′-azobis(isobutyronitrile)

  通过在Et 3 N，3HF / CH 3 CN中对甲基苄基磺酸盐，酯和亚硝酸盐进行阳极氧化，可在苄基位置上进行区域选择性官能化（形成苄基氟化物和乙酰胺）。为了检查化学选择性的决定因素。将其与在CCl 4中通过1,3-二溴5,5-二甲基乙内酰脲（DBH）/2.2'-偶氮二（异丁腈）（AIBN）溴化相同化合物获得的结果进行了比较。
• [EN] SPIRODIHYDROBENZOFURANS AS MODULATORS OF CHEMOKINE RECEPTORS<br/>[FR] COMPOSÉS DE SPIRODIHYDROBENZOFURANE COMME MODULATEURS DE RÉCEPTEURS DES CHIMIOKINES
  申请人：GLAXO GROUP LTD

  公开号：WO2009061881A1

  公开（公告）日：2009-05-14

  The present invention relates to a compound of the following formula: or a pharmaceutically acceptable salt thereof, wherein R1 -R4, R8, R9, Y, m, n, and p are defined. Compounds and compositions of the present invention are useful, for example, for the treatment of atherosclerosis.

  本发明涉及以下式的化合物：或其药学上可接受的盐，其中R1-R4，R8，R9，Y，m，n和p被定义。本发明的化合物和组合物例如可用于动脉粥样硬化的治疗。
• Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles
  作者：Archita Sripada、Christian Wolf

  DOI：10.1021/acs.joc.2c01414

  日期：2022.9.2

  A palladium(phosphinoxazoline) catalyzed method for asymmetric allylic alkylation of α-aryl-α-fluoroacetonitriles is introduced. This reaction achieves C–C bond formation and incorporation of two adjacent chirality centers with moderate to good yields, high enantioselectivities, and up to 15:1 dr.

  介绍了钯(膦恶唑啉)催化α-芳基-α-氟乙腈的不对称烯丙基烷基化反应的方法。该反应实现了 C-C 键的形成和两个相邻手性中心的结合，具有中等至良好的产率、高对映选择性和高达 15:1 dr。
• FLORIN, C.;CHANTEGREL, J.;CHARLON, C.;MARSURA, A.;LUU-DUC, C., ANN. PHARM. FR., 1985, 43, N 6, 595-599
  作者：FLORIN, C.、CHANTEGREL, J.、CHARLON, C.、MARSURA, A.、LUU-DUC, C.

  DOI：——

  日期：——