(Z)-3-(4-fluorophenyl)-2-methoxyacrylic acid | 1357448-07-7

• 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: (Z)-3-(4-fluorophenyl)-2-methoxyacrylic acid
• 英文别名: (Z)-3-(4-fluorophenyl)-2-methoxyprop-2-enoic acid
• CAS: 1357448-07-7
• 化学式: C₁₀H₉FO₃
• 分子量: 196.178
• InChiKey: MMTQODUTQLPAJN-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯基-1,3,4-噁二唑 、 (Z)-3-(4-fluorophenyl)-2-methoxyacrylic acid 在 bis(acetylacetonato)palladium(II) 、 copper carbonate hydroxide 、 1,2-双(二苯基膦)乙烷 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 12.0h， 以92%的产率得到
  参考文献：
  名称：

  Pd-Catalyzed Regioselective Decarboxylative/C–H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers

  摘要：

  A direct introduction of vinyl ethers into C-H bond of heterocycles is reported. For this purpose, decarboxylative direct C-H cross-coupling of 1,3-diazoles with alpha-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various alpha-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.

  DOI：

  10.1021/acscatal.7b01330
• 作为产物：
  描述：

  2-methyl-4-(4-fluorophenylmethylene)-5(4H)-oxazolone 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.5h， 生成 (Z)-3-(4-fluorophenyl)-2-methoxyacrylic acid
  参考文献：
  名称：

  Synthesis of novel cinnamanilides as potential immunosuppressive agents

  摘要：

  A series of new cinnamanilides (6-40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 +/- 0.33 and 0.94 +/- 0.13 mu M) without significant cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.027

文献信息

• Synthesis of novel cinnamanilides as potential immunosuppressive agents
  作者：Lei Shi、Lu Wang、Zhi Wang、Hai-Liang Zhu、Qiao Song

  DOI：10.1016/j.ejmech.2011.10.027

  日期：2012.1

  A series of new cinnamanilides (6-40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 +/- 0.33 and 0.94 +/- 0.13 mu M) without significant cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Pd-Catalyzed Regioselective Decarboxylative/C–H α-Alkoxyalkenylation of Heterocycles Using α-Carboxyvinylethers
  作者：Jean-Baptiste E. Y. Rouchet、Mahmoud Hachem、Cédric Schneider、Christophe Hoarau

  DOI：10.1021/acscatal.7b01330

  日期：2017.8.4

  A direct introduction of vinyl ethers into C-H bond of heterocycles is reported. For this purpose, decarboxylative direct C-H cross-coupling of 1,3-diazoles with alpha-carboxyvinyl ethers as coupling partners was achieved under Pd(0)/Cu(I) cooperative catalysis to produce various alpha-heteroarylated vinylethers. This methodology was applied to the innovative production of heteroarylated enolizable ketones and naturally occurring bis-oxa(thia)zoles.