(E)-3-(4-Fluoro-phenyl)-but-2-enoic acid methyl ester | 198889-33-7

• 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: (E)-3-(4-Fluoro-phenyl)-but-2-enoic acid methyl ester
• 英文别名: methyl 3-(4-fluorophenyl)but-2-enoate
• CAS: 198889-33-7
• 化学式: C₁₁H₁₁FO₂
• 分子量: 194.206
• InChiKey: GNJGRAWNPUCVSX-UHFFFAOYSA-N

物化性质

• 沸点：
  257.1±9.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-3-(4-Fluoro-phenyl)-but-2-enoic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 3-(4-fluorophenyl)butanoic acid
  参考文献：
  名称：

  Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells

  摘要：

  In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.050
• 作为产物：
  描述：

  巴豆酸甲酯 、 对溴氟苯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 顺式,顺式,顺式-1,2,3,4-四[(二苯基膦)甲基]环戊烷 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以88%的产率得到(E)-3-(4-Fluoro-phenyl)-but-2-enoic acid methyl ester
  参考文献：
  名称：

  四膦/钯催化的芳基卤化物与双取代烯烃的Heck反应

  摘要：

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化巴豆酸甲酯，肉桂酸乙酯，甲基丙烯酸甲酯或α等二取代烯烃的Heck反应-甲基苯乙烯与各种芳基卤化物。在1，2-二取代的烯烃的存在下，反应的立体选择性强烈取决于烯烃的取代基。添加到巴豆酸甲酯中可以得到高达97％的选择性，有利于E-异构体。用1，1-二取代的烯烃获得甲基丙烯酸甲酯或α-甲基苯乙烯的产物混合物。

  DOI：

  10.1016/j.tetlet.2003.09.092

文献信息

• Diastereo‐ and Enantioselective Construction of Vicinal All‐Carbon Quaternary Stereocenters via Iridium/Europium Bimetallic Catalysis
  作者：Wei Wang、Fangqing Zhang、Yangbin Liu、Xiaoming Feng

  DOI：10.1002/anie.202208837

  日期：2022.9.26

  dual-metal-catalyzed asymmetric allylic alkylation reaction has been developed by makig use of challenging trisubstituted allylic esters and nucleophilic C3-substituted oxindole derivatives. A variety of allylated products bearing vicinal all-carbon quaternary stereocenters could be obtained in good yields with high to excellent diastereoselectivities (up to 20 : 1 dr) and enantioselectivities (up to 99 % ee)

  通过使用具有挑战性的三取代烯丙基酯和亲核 C3-取代的羟吲哚衍生物，开发了一种前所未有的 Ir/Eu 双金属催化的不对称烯丙基烷基化反应。可以以良好的收率获得具有高至优异的非对映选择性（高达 20 : 1 dr）和对映选择性（高达 99 % ee）的各种带有连位全碳四元立体中心的烯丙基化产物。
• Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes
  作者：Isabelle Kondolff、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2003.09.092

  日期：2003.11

  cyclopentane/[PdCl(C3H5)]2 efficiently catalyses the Heck reaction of disubstituted alkenes such as methyl crotonate, ethyl cinnamate, methyl methacrylate or α-methylstyrene with a variety of aryl halides. In the presence of 1,2-disubstituted alkenes the stereoselectivities of the reactions strongly depend on the substituents of the alkenes. Selectivities up to 97% in favor of E-isomers can be obtained

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化巴豆酸甲酯，肉桂酸乙酯，甲基丙烯酸甲酯或α等二取代烯烃的Heck反应-甲基苯乙烯与各种芳基卤化物。在1，2-二取代的烯烃的存在下，反应的立体选择性强烈取决于烯烃的取代基。添加到巴豆酸甲酯中可以得到高达97％的选择性，有利于E-异构体。用1，1-二取代的烯烃获得甲基丙烯酸甲酯或α-甲基苯乙烯的产物混合物。
• Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells
  作者：Giulia Stazi、Cecilia Battistelli、Valentina Piano、Roberta Mazzone、Biagina Marrocco、Sara Marchese、Sharon M. Louie、Clemens Zwergel、Lorenzo Antonini、Alexandros Patsilinakos、Rino Ragno、Monica Viviano、Gianluca Sbardella、Alessia Ciogli、Giancarlo Fabrizi、Roberto Cirilli、Raffaele Strippoli、Alessandra Marchetti、Marco Tripodi、Daniel K. Nomura、Andrea Mattevi、Antonello Mai、Sergio Valente

  DOI：10.1016/j.ejmech.2018.11.050

  日期：2019.2

  In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. (C) 2018 Elsevier Masson SAS. All rights reserved.