(E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid | 73867-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid
• 英文别名: (E)-2,4-dimethoxy-α-(4-methoxyphenyl)cinnamic acid；(E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoic acid
• CAS: 73867-36-4
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: BXRCPKFLQXZVIP-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid 在 lithium aluminium tetrahydride 、 四溴化碳 、 C₅₆H₇₂IrNOP 、 氢气 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0~70.0 ℃ 、1.22 MPa 条件下， 反应 104.25h， 生成 雌马酚
  参考文献：
  名称：

  Enantioselective iridium-catalyzed hydrogenation of α-arylcinnamic acids and synthesis of (S)-equol

  摘要：

  By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of alpha-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01 mol %), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99% ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4% overall yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.118
• 作为产物：
  描述：

  对甲氧基苯乙酸 、 2,4-二甲氧基苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 2.0h， 以81%的产率得到(E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid
  参考文献：
  名称：

  Enantioselective iridium-catalyzed hydrogenation of α-arylcinnamic acids and synthesis of (S)-equol

  摘要：

  By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of alpha-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01 mol %), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99% ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4% overall yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.118

文献信息

• The Oxidation of (<i>E</i>)-α-Phenylcinnamic Acids with Manganese(III) Acetate
  作者：Kazuki Oishi、Kazu Kurosawa

  DOI：10.1246/bcsj.53.179

  日期：1980.1

  The oxidation of eight (E)-α-phenylcinnamic acids with manganese(III) acetate in boiling acetic acid containing acetic anhydride gave 3-phenylcoumarins, 3-phenyl-l-oxaspiro[4.5]deca-3,7,9-triene-2,6-diones, 2-phenylbenzofurans, 3-(acetoxymethyl)-2-phenylbenzofurans, 3-formyl-2-phenylbenzofuran, 2-acetoxy-2-phenyl-3 (2H)-benzofuranones, (Z)-α-acetoxystilbenes, 2-acetoxy-1,2-diphenylethanones, 5-acetoxy-4

  八种 (E)-α-苯基肉桂酸与乙酸锰 (III) 在沸腾的乙酸酐中氧化得到 3-苯基香豆素、3-苯基-1-氧杂螺[4.5]deca-3,7,9-triene- 2,6-二酮、2-苯基苯并呋喃、3-(乙酰氧基甲基)-2-苯基苯并呋喃、3-甲酰基-2-苯基苯并呋喃、2-乙酰氧基-2-苯基-3 (2H)-苯并呋喃酮、(Z)-α-乙酰氧基芪、2-乙酰氧基-1,2-二苯基乙酮、5-乙酰氧基-4,5-二苯基-2 (5H)-呋喃酮和二苯基乙炔。讨论了反应途径。
• OISHI KAZUKI; KUROSAWA KAZU, BULL. CHEM. SOC., JAP., 1980, 53, NO 1, 179-184,
  作者：OISHI KAZUKI、 KUROSAWA KAZU

  DOI：——

  日期：——
• Enantioselective iridium-catalyzed hydrogenation of α-arylcinnamic acids and synthesis of (S)-equol
  作者：Shuang Yang、Shou-Fei Zhu、Can-Ming Zhang、Song Song、Yan-Bo Yu、Shen Li、Qi-Lin Zhou

  DOI：10.1016/j.tet.2012.03.118

  日期：2012.7

  By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of alpha-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01 mol %), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99% ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4% overall yield. (C) 2012 Elsevier Ltd. All rights reserved.