3-(3,4-dimethoxyphenyl)-2-phenylpropenoic acid | 54208-12-7

• 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: 3-(3,4-dimethoxyphenyl)-2-phenylpropenoic acid
• 英文别名: 3-(3,4-dimethoxy-phenyl)-2-phenyl-acrylic acid；3'.4'-Dimethoxy-stilben-α-carbonsaeure；3-(3,4-Dimethoxy-phenyl)-2-phenyl-acrylsaeure；3.4-Dimethoxy-α-phenyl-zimtsaeure；3-(3,4-Dimethoxyphenyl)-2-phenylprop-2-enoic acid
• CAS: 54208-12-7
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: MQBXTTFTYGOQNR-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C(Solv: acetic acid (64-19-7))
• 沸点：
  412.3±40.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-2-phenylpropenoic acid 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 (Z)-3-(3,4-Dimethoxy-phenyl)-2-phenyl-prop-2-en-1-ol
  参考文献：
  名称：

  Gierer,J. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 717 - 729

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium phenylacetate 、 3,4-二甲氧基苯甲醛 在 乙酸酐 作用下， 生成 3-(3,4-dimethoxyphenyl)-2-phenylpropenoic acid
  参考文献：
  名称：

  Kauffmann, Chemische Berichte, 1919, vol. 52, p. 1431

  摘要：

  DOI：

文献信息

• Intramolecular Biaryl Oxidative Coupling of Stilbenes by Vanadium Oxytrichloride (VOCl₃): Facile Synthesis of Substituted Phenanthrene Derivatives
  作者：Zhong Jin、Qingmin Wang、Runqiu Huang

  DOI：10.1081/scc-120027245

  日期：2004.12.31

  Abstract Vanadium oxytrichloride (VOCl3) has proven to be a highly efficient reagent for intramolecular biaryl oxidative coupling reaction of electron‐rich stilbenes. Accordingly, a mild and efficient route to phenanthrene derivatives from stilbenes oxygenated is developed.

  摘要 三氯氧化钒 (VOCl3) 已被证明是富电子二苯乙烯分子内联芳基氧化偶联反应的高效试剂。因此，开发了一种从二苯乙烯氧化得到菲衍生物的温和有效的途径。
• Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues
  作者：De-Jun Ding、Xiao-Yan Cao、Fang Dai、Xiu-Zhuang Li、Guo-Yun Liu、Dong Lin、Xing Fu、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.foodchem.2012.05.074

  日期：2012.12

  Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants. (C) 2012 Elsevier Ltd. All rights reserved.
• Gierer,J. et al., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 717 - 729
  作者：Gierer,J. et al.

  DOI：——

  日期：——
• Kauffmann, Chemische Berichte, 1919, vol. 52, p. 1431
  作者：Kauffmann

  DOI：——

  日期：——