2-benzoxy-3-phenylpropenoic acid | 107056-59-7

• 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: 2-benzoxy-3-phenylpropenoic acid
• 英文别名: (Z)-2-(benzyloxy)-3-phenylacrylic acid；α-benzyloxy-trans-cinnamic acid；α-Benzyloxy-trans-zimtsaeure；(Z)-3-phenyl-2-phenylmethoxyprop-2-enoic acid
• CAS: 107056-59-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: FUMXCJDLZWYSSK-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoxy-3-phenylpropenoic acid 在 copper(II) carbonate 、 三氯化硼 、 palladium dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  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：

  (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 在 溶剂黄146 作用下， 生成 2-benzoxy-3-phenylpropenoic acid
  参考文献：
  名称：

  PHENYLPYRUVIC ACID DERIVATIVES AS ENZYME INHIBITORS: THERAPEUTIC POTENTIAL ON MACROPHAGE MIGRATION INHIBITORY FACTOR

  摘要：

  Phenylpyruvic acid derivatives are obtained by hydrolysing aromatic Z/E azlactones. Keto tautomers interact with enzyme systems such as phenylalanine dehydrogenase or carboxypeptidase A whereas enol tautomers are potential inhibitors on the phenylpyruvate tautomerase activity catalysed by Macrophage Migration Inhibitory Factor (MIF). MIF being a key molecule in immune and inflammatory processes several structures with reasonable interaction with MIF and protocol for specific synthesis are presented.

  DOI：

  10.1007/s00044-004-0102-y

文献信息

• Enantioselective Hydrogenation of α-Aryloxy and α-Alkoxy α,β-Unsaturated Carboxylic Acids Catalyzed by Chiral Spiro Iridium/Phosphino-Oxazoline Complexes
  作者：Shen Li、Shou-Fei Zhu、Jian-Hua Xie、Song Song、Can-Ming Zhang、Qi-Lin Zhou

  DOI：10.1021/ja909810k

  日期：2010.1.27

  The iridium-catalyzed highly enantioselective hydrogenation of alpha-aryloxy and alpha-alkoxy-substituted alpha,beta-unsaturated carboxylic acids was developed. By using chiral spiro phosphino-oxazoline ligands, the hydrogenation proceeded smoothly to produce various alpha-aryloxy- and alpha-alkoxy-substituted carboxylic acids with extremely high enantioselectivities (ee up to 99.8%) and reactivities

  开发了铱催化的α-芳氧基和α-烷氧基取代的α，β-不饱和羧酸的高度对映选择性氢化。通过使用手性螺环膦基-恶唑啉配体，氢化反应顺利进行，在温和的条件下产生了具有极高对映选择性（ee 高达 99.8%）和反应性（TON 高达 10,000）的各种 α-芳氧基和 α-烷氧基取代的羧酸. α-苄氧基取代的α，β-不饱和酸的氢化为经过简单脱保护后合成手性α-羟基酸提供了一种有效的替代方法。基于不饱和酸与铱金属中心的配位模型，提出了一种涉及 Ir(I) 和 Ir(III) 之间催化循环的机制。催化循环的合理性，以烯烃二氢化物配合物为关键中间体，得到了氘标记研究的支持。催化剂单晶的 X 射线衍射分析表明，由螺环膦基-恶唑啉配体产生的刚性和空间位阻手性环境是使催化剂获得优异手性辨别力的重要因素。根据催化剂结构和产物构型提出了手性诱导模型。
• �ber Kondensationen von aromatischen Aldehyden mit Glykols�urederivaten
  作者：Th. Gr�ger、E. Waldmann

  DOI：10.1007/bf00898758

  日期：——
• 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.
• PHENYLPYRUVIC ACID DERIVATIVES AS ENZYME INHIBITORS: THERAPEUTIC POTENTIAL ON MACROPHAGE MIGRATION INHIBITORY FACTOR
  作者：Alain J.M. Carpy、Petrus P. Haasbroeck、Douglas W. Oliver

  DOI：10.1007/s00044-004-0102-y

  日期：2004.10

  Phenylpyruvic acid derivatives are obtained by hydrolysing aromatic Z/E azlactones. Keto tautomers interact with enzyme systems such as phenylalanine dehydrogenase or carboxypeptidase A whereas enol tautomers are potential inhibitors on the phenylpyruvate tautomerase activity catalysed by Macrophage Migration Inhibitory Factor (MIF). MIF being a key molecule in immune and inflammatory processes several structures with reasonable interaction with MIF and protocol for specific synthesis are presented.