α-(Fluorophenyl)acetonitrile | 10036-43-8

• 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: α-(Fluorophenyl)acetonitrile
• 英文别名: 2-fluoro-2-phenylacetonitrile
• CAS: 10036-43-8
• 化学式: C₈H₆FN
• mdl: MFCD26407968
• 分子量: 135.141
• InChiKey: YNKQLRDKQOEOGC-UHFFFAOYSA-N

物化性质

• 沸点：
  65-70 °C(Press: 3 Torr)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  α-(Fluorophenyl)acetonitrile 在 硫酸 作用下， 反应 3.0h， 生成 Α-氟苯基乙酸
  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：

  2-fluoro-2-phenylacetyl chloride 在 氨 、 phosphorus pentoxide 作用下， 以 水 为溶剂， 100.0~107.0 ℃ 、466.63 Pa 条件下， 生成 α-(Fluorophenyl)acetonitrile
  参考文献：
  名称：

  Cavalleri; Bellasio; Gallo, Farmaco, Edizione Scientifica, 1968, vol. 23, # 12, p. 1127 - 1140

  摘要：

  DOI：

文献信息

• Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters
  作者：Ransheng Ding、Zeus A. De los Santos、Christian Wolf

  DOI：10.1021/acscatal.8b05164

  日期：2019.3.1

  Diastereodivergent and enantioselective conversion of isatin ketimines to α-fluoro-β-aminonitriles with vicinal tetrasubstituted stereocenters is achieved by a chiral copper complex/guanidine base catalyzed Mannich reaction with proper choice of the bisphosphine ligand. The reaction is broad in scope, scalable, and provides efficient access to a series of 3-aminoindolinones exhibiting a quaternary

  Diastereodivergent和靛红酮亚胺到α氟-β氨基腈与四取代的邻位立体中心的对映选择性转化是通过手性铜络合物/胍碱催化的实现与双膦配体的适当选择曼尼希反应。该反应的范围宽广，可扩展，并提供了高产率和立体选择性的一系列3-氨基吲哚酮的有效通道，这些3-氨基吲哚酮具有季碳-氟立体中心。曼尼希反应产物选择性转化成多功能的3-氨基羟吲哚，而不会削弱对映体和非对映体的纯度，这突出了合成的实用性。
• Selective electrolytic fluorinations in 70% HF/30% pyridine
  作者：Sarah M. Lee、Jamie M. Roseman、C. Blair Zartman、Eamonn P. Morrison、Sean J. Harrison、Corrie A. Stankiewicz、W.J. Middleton

  DOI：10.1016/0022-1139(95)03379-3

  日期：1996.3

  The selective fluorination of compounds containing benzylic hydrogen atoms was accomplished by electrolysis in a mixture of 70% HF and 30% pyridine (Olah's reagent) using a square wave alternating current (1.76–2.75 V, 0.02–0.05 Hz) and Pt electrodes. This method can be used in the laboratory to prepare conveniently gram-size quantities of monofluorinated products. An ion radical mechanism has been

  使用方波交流电（1.76-2.75 V，0.02-0.05 Hz）和Pt电极，在70％HF和30％吡啶（Olah试剂）的混合物中进行电解，即可完成含苄基氢原子的化合物的选择性氟化。此方法可在实验室中用于方便地制备克级量的单氟化产物。已经提出了离子自由基机理。
• Mono et difluoration electrochimiques de groupes benzyliques
  作者：Eliane Laurent、Bernard Marquet、Robert Tardivel

  DOI：10.1016/s0040-4020(01)89079-7

  日期：——

  a fluorinating reagent allowed to introduce a fluorine atom in α position of electron withdrawing group via carbocation + (ECBECN mechanism). Whatever the E group monofluorides are obtained in good yields from paramethoxy derivatives (R=p-OCH3). In this case, by raising the potential of working electrode after the monofluorination step, gem difluorides can be directly prepared from 1. When the substituent

  以CH 3 CN为溶剂，以Et 3 N，3HF为氟化剂，对苄基化合物进行阳极氧化，通过碳正离子+（EC B EC N机理）在吸电子基团的α位置引入氟原子。从对甲氧基衍生物（R ＝ p-OCH 3）以高收率获得任何E基团一氟化物。在这种情况下，通过在单氟化步骤之后提高工作电极的电势，可以直接从1制备二氟化宝石。当苯环的取代基与甲氧基不同时，氟化物2和乙酰胺的混合物 通常可以得到H 2 O 3，这两种化合物的比例与阳离子稳定性有关。
• 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine: a new selective fluorinating agent
  作者：Viacheslav A. Petrov、Steve Swearingen、Wonpyo Hong、W. Chris Petersen

  DOI：10.1016/s0022-1139(01)00372-4

  日期：2001.6

  The title compound has been prepared in 96–98% yield by the reaction of tetrafluoroethylene and dimethylamine. 1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine (1) is found to be an effective reagent for the conversion of alcohols into alkyl fluorides. Reaction of 1 and primary alcohols proceeds with high yield formation of the corresponding alkyl fluorides at elevated temperature. However, the reaction

  通过四氟乙烯和二甲胺的反应，可以制备标题化合物，产率为96–98％。发现1,1,2,2-四氟乙基-N，N-二甲基胺（1）是将醇转化为烷基氟化物的有效试剂。1和伯醇的反应在高温下以高收率形成了相应的烷基氟化物。但是，仲醇和叔醇的反应在0–10°C下迅速发生，产生相应的烷基氟化物作为主要产物以及一些烯烃。
• Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
  作者：De-Yin Chen、Shuai Song、Ling-Yan Chen、Xinfeng Ren、Ya Li

  DOI：10.1016/j.tetlet.2021.152919

  日期：2021.3

  An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to

  通过2-氟-2-芳基乙腈的有机催化迈克尔加成反应，已开发出一种有效的合成各种含氟立构中心的2-芳基乙腈的方法。该方案使用廉价的有机催化剂（DBU），并具有广泛的底物范围：α，β-不饱和酮，酯，腈和砜均已成功反应。重要的是，事实证明水是该反应的良好溶剂。