(E)-2-fluoro-3-phenyl-acrylonitrile | 140137-13-9

• 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: (E)-2-fluoro-3-phenyl-acrylonitrile
• 英文别名: (E)-2-fluoro-3-phenylacrylonitrile；(E)-α-fluorocinnamonitrile；(E)-2-fluoro-3-phenylprop-2-enenitrile
• CAS: 140137-13-9
• 化学式: C₉H₆FN
• 分子量: 147.152
• InChiKey: GKUORMZUZQIKEB-RMKNXTFCSA-N

物化性质

• 沸点：
  224.8±25.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基丙炔腈 生成 (E)-2-fluoro-3-phenyl-acrylonitrile
  参考文献：
  名称：

  COUSSEAU J.; ALBERT P., BULL. SOC. CHIM. FR.,(1986) N 6, 910-915

  摘要：

  DOI：

文献信息

• Nucleophilic Substitution of <i>gem</i>-Difluoroalkenes with TMSNu Promoted by Catalytic Amounts of Cs₂CO₃
  作者：Ling-Feng Jiang、Bing-Tao Ren、Bin Li、Guang-Yi Zhang、Yi Peng、Zhen-Yu Guan、Qing-Hai Deng

  DOI：10.1021/acs.joc.9b00999

  日期：2019.6.7

  The efficient and practical nucleophilic cyanation and trifluoromethylation with appropriate trimethylsilyl nucleophiles were developed. Catalytic amounts of cheap and nontoxic Cs2CO3 were used to maintain a sufficiently high concentration of nucleophilic anion (CN– or CF3–) which could begin the catalytic cycle. The present methodologies provide diverse functionalized monofluoroalkenes bearing a cyano

  开发了有效和实用的亲核氰化和三氟甲基化反应以及适当的三甲基甲硅烷基亲核试剂。廉价和无毒性的Cs的催化量的2 CO 3被用来维持亲核阴离子（CN的足够高的浓度-或CF 3 - ），其可以开始催化循环。本方法提供了带有氰基和三氟甲基的各种官能化的单氟烯烃，具有优异至中等的立体选择性。
• Fluoro-Julia Olefination as a Mild, High-Yielding Route to α-Fluoro Acrylonitriles
  作者：Maria del Solar、Arun K. Ghosh、Barbara Zajc

  DOI：10.1021/jo801235x

  日期：2008.11.7

  Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl alpha-(1,3- benzothiazol-2-ylsulfanyl)-alpha-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile in the presence of DBU leading to alpha-fluoro acrylonitriles in high yields and with good Z-stereoselectivity. Lowering of reaction temperature increases the Z selectivity.
• α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones
  作者：Jan Hein van Steenis、Adrianus M.C.H van den Nieuwendijk、Arne van der Gen

  DOI：10.1016/j.jfluchem.2003.11.001

  日期：2004.1

  alpha-Fluoroacrylonitriles 2 were synthesized in moderate to good yields by Homer-Wittig (HW) reaction of aldehydes and ketones with (diphenylphosphinoyl)fluoroacetonitrile (1), prepared in situ from commercially available fluoroacetonitrile and diphenylphosphinyl chloride. New synthetic applications of 2 are presented with the one-pot conversion into 2-fluoroallylamines 6 and C-(1-fluorovinyl)nitrones 8 through a diisobutylaluminum hydride (DIBALH)-reduction transimination protocol. The scope and limitations of this procedure are discussed. (C) 2003 Elsevier B.V. All rights reserved.
• Xu, Ze-Qi; DesMarteau, Darryl D., Journal of the Chemical Society. Perkin transactions I, 1992, # 3, p. 313 - 316
  作者：Xu, Ze-Qi、DesMarteau, Darryl D.

  DOI：——

  日期：——
• Stereoselective cyanation of β-bromo-β-fluorostyrenes using potassium cyanide and promoted by (CH3CN)4Cu+ BF4−
  作者：Said Eddarir、Mohammed Kajjout、Christian Rolando

  DOI：10.1016/j.tet.2011.10.111

  日期：2012.1

  A general method for the synthesis of alpha-fluorocinnamonitrile based on the stereoselective reaction between beta-bromo-beta-fluorostyrene and potassium cyanide, promoted by (CH3CN)(4)Cu+ BF4- in 1-methyl-2-pyrrolidinone (NMP), is described. (C) 2011 Elsevier Ltd. All rights reserved.