methyl (Z)-3-fluoro-3-phenyl-2-propenoate | 82754-33-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (Z)-3-fluoro-3-phenyl-2-propenoate
• 英文别名: (Z)-methyl 3-phenyl 3-fluoro 2-propenoate；methyl (Z)-3-fluoro-3-phenylpropenoate；methyl (Z)-3-fluoro-3-phenylprop-2-enoate
• CAS: 82754-33-4
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: SSENYSUWHAKBLS-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-fluoro-3-phenyl-2-propenoate 、 二异丁基氢化铝 以80%的产率得到
  参考文献：
  名称：

  GILLET, J. P.;SAUVETRE, R.;NORMANT, J. F., SYNTHESIS, BRD, 1982, N 4, 297-301

  摘要：

  DOI：
• 作为产物：
  描述：

  phenylmagnesium bromide 在 草酰氯 、 甲基锂 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (Z)-3-fluoro-3-phenyl-2-propenoate
  参考文献：
  名称：

  Carboxylation of 2,2-Difluorovinyllithium: A New General Synthesis of α,β-Unsaturated β-Fluoroalcohols, -ketones, and -acids

  摘要：

  DOI：

  10.1055/s-1982-29787

文献信息

• Mono-hydrofluorination of electrophilic alkynes by the liquid biphasic CsF–H₂O–DMF system (DMF = N,N-dimethylformamide)
  作者：Alain Gorgues、Dominique Stéphan、Jack Cousseau

  DOI：10.1039/c39890001493

  日期：——

  CsF induces the addition of HF in fair yields to activated acetylenic triple bonds in a DMF–water biphasic medium (DMF = N,N-dimethylformamide); in a homogeneous DMF–water mixture, no addition is observed.

  CsF在DMF-水双相介质（DMF = N，N-二甲基甲酰胺）中以合理的产率将HF加到活化的炔三键上。在均匀的DMF与水的混合物中，未观察到添加物。
• Tetrabutylammonium and polymer-supported dihydrogentrifluoride: new hydrofluorinating reagents for electrophilic alkynes
  作者：Patrice Albert、Jack Cousseau

  DOI：10.1039/c39850000961

  日期：——

  Tetrabutylammonium and polymer-supported dihydrogentrifluoride are readily accessible reagents which allow addition of HF to activated carbon–carbon triple bonds, thus leading to functional fluoroalkenes in good yields.

  四丁基铵和聚合物负载的三氟化二氢是易于获得的试剂，可以将HF加到活性碳-碳三键上，从而以高收率得到功能性的氟代烯烃。
• Stereoselective synthesis of (Z)-β-fluoro-α,β-unsaturated esters from (Z)-2-fluoro-1-alkenyliodonium salts
  作者：Masanori Yoshida、Ayumu Komata、Shoji Hara

  DOI：10.1016/j.jfluchem.2003.11.025

  日期：2004.4

  (Z)-β-Fluoro-α,β-unsaturated esters were stereoselectively synthesized from (Z)-2-fluoro-1-alkenyliodonium salts by the Pd-catalyzed methoxycarbonylation reaction. The reaction proceeded at room temperature and various functional groups on the substrate can tolerate the reaction conditions.

  由（Z）-2-氟-1-烯基碘鎓盐通过Pd催化的甲氧基羰基化反应立体选择性地合成（Z）-β-氟-α，β-不饱和酯。反应在室温下进行，并且底物上的各种官能团可以耐受反应条件。
• Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts
  作者：Masanori Yoshida、Ayumu Komata、Shoji Hara

  DOI：10.1016/j.tet.2006.05.085

  日期：2006.9

  Stereoselective synthesis of fluoroalkenes is described. (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl(phenyl)iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N-3HF. Pd-catalyzed cross-coupling reactions using 1 gave (Z)-2-fluoro-l-alkene derivatives in moderate yields. The treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-l-alkene derivatives were synthesized in good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Cousseau, Jack; Albert, Patrice, Bulletin de la Societe Chimique de France, 1986, # 6, p. 910 - 915
  作者：Cousseau, Jack、Albert, Patrice

  DOI：——

  日期：——