(2Z)-3-(3-bromo-2,4,6-trimethylphenyl)propenoic acid

• 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: (2Z)-3-(3-bromo-2,4,6-trimethylphenyl)propenoic acid
• 英文别名: 3-(3-bromo-2,4,6-trimethylphenyl)propenoic acid；(Z)-3-(3-bromo-2,4,6-trimethylphenyl)prop-2-enoic acid
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: QHCPAXDSZNUJRR-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-1,3,5-三甲基苯 、 丙炔酸 在 potassium tetrachloroplatinate 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 反应 40.0h， 以88%的产率得到(2Z)-3-(3-bromo-2,4,6-trimethylphenyl)propenoic acid
  参考文献：
  名称：

  K 2 PtCl 4 / AgOTf催化剂在丙酸与未活化和活化的芳烃反应中具有很高的加氢芳化活性

  摘要：

  在钯和铂催化剂中，混合催化剂K 2 PtCl 4 / AgOTf显示出最高的丙酸加氢芳基化活性。该催化剂可有效地用较少的反应性苯进行加氢芳基化反应，以高收率得到顺式肉桂酸。用甲苯进行氢芳基化反应比使用苯进行氢芳基化反应的收率更高，并导致邻位/对位取向，并且几乎具有统计比例，这表明该结果非常接近于用甲基溴或对硝基苄基进行的Friedel-Crafts烷基化反应的结果。氯化物。在K 2存在下，丙酸与其他富电子芳烃的氢芳基化反应有效进行在三氟乙酸中的PtCl 4 / AgOTf催化剂以良好或高收率形成顺式肉桂酸。该方法也适用于丙酸乙酯的氢芳基化。

  DOI：

  10.1016/j.jorganchem.2009.07.008

文献信息

• Efficient and selective hydroarylation of propiolic acids and their esters with arenes catalyzed by a PtCl2/AgOTf system
  作者：Juzo Oyamada、Tsugio Kitamura

  DOI：10.1016/j.tetlet.2005.03.179

  日期：2005.5

  PtCl2/AgOTf-catalyzed hydroarylation of ethyl propiolate proceeded effectively to give ethyl (2Z)-cinnamate derivatives in good to high yields, without the formation of diethyl (1E,3Z)-4-arylbuta-1,3-diene-1,3-dicarboxylates that was observed in Pd(OAc)2-catalyzed reaction. Especially, PtCl2/AgOTf-catalyzed hydroarylation of propiolic acids proceeded effectively to give (2Z)-cinnamic acids exclusively.

  PtCl2/AgOTf 催化的丙炔酸乙酯的加氢芳基化有效地进行，以良好至高产率得到 (2Z)-肉桂酸乙酯衍生物，而没有形成 (1E,3Z)-4-arylbuta-1,3-diene-1,3 二乙基酯-在 Pd(OAc)2 催化反应中观察到的二羧酸盐。尤其是，PtCl2/AgOTf 催化的丙炔酸加氢芳基化有效地进行，仅得到 (2Z)-肉桂酸。
• K₂PtCl₄/AgOTf as a Highly Active Catalyst for Hydroarylation of Propiolic Acids with Arenes
  作者：Juzo Oyamada、Tsugio Kitamura

  DOI：10.1246/cl.2005.1430

  日期：2005.10

  A new and efficient K2PtCl4/AgOTf catalyst for the hydroarylation of propiolic acid was found. The hydroarylation of propiolic acids gave predominantly (Z)-cinnamic acid derivatives in high yields. The K2PtCl4/AgOTf catalyst showed a high activity to less reactive benzene.

  发现了一种新型高效的 K2PtCl4/AgOTf 催化剂用于丙炔酸的氢芳基化反应。丙炔酸的氢芳基化主要产生高产率的 (Z)-肉桂酸衍生物。K2PtCl4/AgOTf 催化剂对反应性较低的苯具有很高的活性。
• Catalytic hydroarylation of alkynes with arenes in the presence of FeCl3 and AgOTf
  作者：Takuya Hashimoto、Shahajahan Kutubi、Takayuki Izumi、Ataur Rahman、Tsugio Kitamura

  DOI：10.1016/j.jorganchem.2010.08.009

  日期：2011.1

  Hydroarylation of propiolic acids with various arenes in TFA proceeded efficiently in the presence of FeCl3/AgOTf catalyst system. In the case of electron-rich arenes, the iron-catalyzed hydroarylation gave cinnamic acids in moderate to high yields. The hydroarylation of phenylacetylene was observed but the catalyst was not effective under the same conditions. (C) 2010 Elsevier B.V. All rights reserved.
• Highly selective hydroarylation of propiolic acid derivatives using a PtCl2/AgOTf catalytic system
  作者：Juzo Oyamada、Tsugio Kitamura

  DOI：10.1016/j.tet.2007.09.076

  日期：2007.12

  Hydroarylation of propiolic acid derivatives with arenes in trifluoroacetic acid efficiently proceeded in the presence Of PtCl2/AgOTf catalyst to give cis-cinnamic acid derivatives in good to high yields. This PtCl2/AgOTf-catalyzed reaction did not afford any 4-arylbuta-1,3-diene-1,3-dicarboxylic acid derivatives formed by Pd(OAc)(2)-catalyzed hydroarylation. The specific optimization of the catalytic hydroarylation and application to electron-rich arenes are reported. (c) 2007 Elsevier Ltd. All rights reserved.
• Iron(III)-catalyzed hydroarylation of propiolic acid with activated arenes
  作者：Takuya Hashimoto、Takayuki Izumi、Md. Shahajahan Kutubi、Tsugio Kitamura

  DOI：10.1016/j.tetlet.2009.11.130

  日期：2010.1

  FeCl3/AgOTf-catalyzed hydroarylation of propiolic acid with electron-rich arenes such as mesitylene, tetramethylbenzene, and pentamethylbenzene in trifluoroacetic acid proceeded to give 3-arylpropenoic acids in moderate to high yields. The same reactions with anisole and 1,4-dimethoxybenzene afforded double hydroarylation products, 3,3-diarylpropionic acids. (C) 2009 Elsevier Ltd. All rights reserved.