(E)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile | 130537-03-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile
• 英文别名: (E)-2-fluoro-3-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 130537-03-0
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: PKMVGCDXOGPZCF-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 1-(2,2-二氟乙烯基)-4-甲氧基苯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 以52%的产率得到(E)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  α-fluoroacrylonitriles的立体选择性合成通过的有机催化氰化宝石-difluoroalkenes和TMSCN †

  摘要：

  开发了宝石-二氟烯烃的有机催化氰化反应。在10摩尔％DBU的催化下，宝石-二氟烯烃与三甲基甲硅烷基氰化物进行亲核加成-β-消除反应，以50-98％的产率提供具有优异Z / E选择性的α-氟代丙烯腈。

  DOI：

  10.1039/c9nj02370d

文献信息

• 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.
• 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.
• Preparation of fluoroalkenes from fluoroacetonitrile
  作者：Timothy B. Patrick、Sourena Nadji

  DOI：10.1016/s0022-1139(00)80371-1

  日期：1990.7
• Stereoselective synthesis of α-fluoroacrylonitriles <i>via</i> organocatalytic cyanation of <i>gem</i>-difluoroalkenes and TMSCN
  作者：Yu-Chuan Ma、Yang Zhang、Cheng-Zhi Gu、Guang-Fen Du、Lin He

  DOI：10.1039/c9nj02370d

  日期：——

  An organocatalytic cyanation reaction of gem-difluoroalkenes was developed. Under the catalysis of 10 mol% DBU, gem-difluoroalkenes undergo a nucleophilic addition-β-elimination reaction with trimethylsilyl cyanide to provide α-fluoroacrylonitriles in 50–98% yields with excellent Z/E selectivity.

  开发了宝石-二氟烯烃的有机催化氰化反应。在10摩尔％DBU的催化下，宝石-二氟烯烃与三甲基甲硅烷基氰化物进行亲核加成-β-消除反应，以50-98％的产率提供具有优异Z / E选择性的α-氟代丙烯腈。