(Z)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile | 130537-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile
• 英文别名: (Z)-2-fluoro-3-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 130537-02-9
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: PKMVGCDXOGPZCF-TWGQIWQCSA-N

物化性质

• 沸点：
  287.2±30.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

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：

  1-(2,2-二氟乙烯基)-4-甲氧基苯 在 copper(II) nitrate trihydrate 、 cesium fluoride 、 双(2-二苯基磷苯基)醚 、 copper dichloride 、 lithium tert-butoxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 (Z)-2-fluoro-3-(4-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  铜催化的对二氟烯烃的立体选择性脱氟硼化和甲硅烷基化

  摘要：

  铜催化的立体选择性defluorinative硼化和硅烷化宝石-difluoroalkenes开发。该方案导致Z型一氟烯基硼和硅烷的排他性形成通常具有良好的效率，且具有广泛的底物范围。通过利用C-B和C-Si键的多功能反应性，可以轻松将形成的产物转化为其他含F分子。实验和理论的机理研究进行了支持烯烃插入/顺-planarβ-F消除途径。

  DOI：

  10.1002/adsc.201701497

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
• Copper-Catalyzed Stereoselective Defluorinative Borylation and Silylation of <i>gem</i> -Difluoroalkenes
  作者：Dong-Hang Tan、E Lin、Wei-Wei Ji、Yao-Fu Zeng、Wen-Xin Fan、Qingjiang Li、Hui Gao、Honggen Wang

  DOI：10.1002/adsc.201701497

  日期：2018.3.1

  The copper‐catalyzed stereoselective defluorinative borylation and silylation of gem‐difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrate scope. The products formed could be readily transformed to other F‐containing molecules by taking advantage of the versatile reactivities of C−B

  铜催化的立体选择性defluorinative硼化和硅烷化宝石-difluoroalkenes开发。该方案导致Z型一氟烯基硼和硅烷的排他性形成通常具有良好的效率，且具有广泛的底物范围。通过利用C-B和C-Si键的多功能反应性，可以轻松将形成的产物转化为其他含F分子。实验和理论的机理研究进行了支持烯烃插入/顺-planarβ-F消除途径。