α-phenyl-4-hydroxy-3-methoxycinnamic acid | 87751-70-0

• 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: α-phenyl-4-hydroxy-3-methoxycinnamic acid
• 英文别名: alpha-Phenyl-4-hydroxy-3-methoxy cinnamic acid；3-(4-hydroxy-3-methoxyphenyl)-2-phenylprop-2-enoic acid
• CAS: 87751-70-0
• 化学式: C₁₆H₁₄O₄
• mdl: MFCD00613516
• 分子量: 270.285
• InChiKey: ARPNBQDBKNKVII-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  410.8±40.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-phenyl-4-hydroxy-3-methoxycinnamic acid 在 N-甲基咪唑 、 碳酸氢钠 作用下， 反应 0.33h， 以91%的产率得到2-甲氧基-4-(2-苯乙烯基)苯酚
  参考文献：
  名称：

  Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes

  摘要：

  A metal-free protocol for decarboxylation of substituted alpha-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.046
• 作为产物：
  描述：

  苯乙酸 、 香草醛 在 乙酸酐 、 三乙胺 作用下， 生成 α-phenyl-4-hydroxy-3-methoxycinnamic acid
  参考文献：
  名称：

  Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

  摘要：

  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.

  DOI：

  10.1016/j.foodchem.2012.05.074

文献信息

• Divergent Reactivity in Cu^II-Catalyzed Oxidative Coupling between Indole/Tryptamine Derivatives and β-Arylacrylic Acids
  作者：Wei Cao、Jinbao Fan、Linyang Yan、Guangyao Zeng、Jinjin Ma、Yajing Wang、Yingjun Zhou、Xu Deng

  DOI：10.1021/acs.orglett.9b03697

  日期：2019.12.6

  Condition-controlled divergent oxidative coupling reactions between indole/tryptamine derivatives and β-arylacrylic acids with the catalysis of copper(II) have been developed. Specifically, a formal Michael addition/dehydration sequence between indoles and β-arylacrylic acids occurred in the presence of catalytic CuBr2 in CH3CN under air, thus affording highly functionalized 2,3-dihydro-1H-pyrrolo[1

  已经开发出条件控制的吲哚/色胺衍生物与β-芳基丙烯酸之间的氧化偶联反应，其催化铜（II）。具体而言，在空气中CH 3 CN中存在催化CuBr 2时，吲哚与β-芳基丙烯酸之间存在正式的迈克尔加成/脱水序列，从而提供了高度官能化的2,3-二氢-1 H-吡咯并[1,2- a ]吲哚。相反，在将氧化剂改变为t BuOOH，将溶剂改变为DCM时，反应过程切换到空前的氧化偶合/环化级联反应，从而选择性地得到四环吡咯并[2,3- b ]二氢吲哚。
• Microwave Induced One Pot Process For The Preparation Of Arylethenes
  申请人：Sinha Kumar Arun

  公开号：US20080045752A1

  公开（公告）日：2008-02-21

  The invention entitled “A Microwave Induced One Pot Process for The Preparation of Arylethenes” provides a method for the preparation of commercially important 2- or 4-hydroxy substituted arylethenes like styrenes or stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted cinnamic acids and their derivatives as well as reagents in the form of base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium acetate, imidazole, methylimidazole and the combination thereof, with or without solvent such as dimethylformamide, dimethylsulfoxide, ethylene glycol, diethylene glycol, acetonitrile, acetone, methyl imidazoles, ionic liquid, water and the like. The reaction time vary from 1 min-12 hrs and yield of the products from 49-76% depending upon the base, acid, substrate source of heating monomode or multimode microwave or conventional. It is important to mention that the presence of 2- or 4-hydroxy substitution at phenyl ring of cinnamic acids and their derivatives is essential requirements towards formation of corresponding arylethenes in one step.

  这项名为“一锅法微波诱导制备芳基乙烯”的发明提供了一种在一个反应器中利用更便宜的底物（2-或4-羟基取代肉桂酸及其衍生物）和碱性试剂（如氢氧化钠，氢氧化钾，氢氧化锂，碳酸氢钠，碳酸钠，碳酸氢钾，碳酸钾，乙酸铵，咪唑，甲基咪唑和它们的组合物）制备商业上重要的2-或4-羟基取代的芳基乙烯（如苯乙烯或苯并乙烯）的方法。反应时间为1分钟至12小时，产率为49-76％，取决于碱性试剂、酸性试剂、底物、加热方式（单模或多模微波或传统方式）等因素。值得一提的是，肉桂酸及其衍生物苯环上的2-或4-羟基取代是制备相应芳基乙烯的必要条件，可以在一个步骤中完成。反应可以在溶剂（如二甲基甲酰胺、二甲基亚砜、乙二醇、二乙二醇、乙腈、丙酮、甲基咪唑、离子液体、水等）存在或不存在的情况下进行。
• Microwave induced one pot process for the preparation of arylethenes
  申请人：Council of Scientific & Industrial Research

  公开号：US07759527B2

  公开（公告）日：2010-07-20

  The invention entitled “A Microwave Induced One Pot Process for The Preparation of Arylethenes” provides a method for the preparation of commercially important 2- or 4-hydroxy substituted arylethenes like styrenes or stilbenes in one pot utilizing cheaper substrates in the form of 2- or 4-hydroxy substituted cinnamic acids and their derivatives as well as reagents in the form of base such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium bicarbonate, potassium carbonate, ammonium acetate, imidazole, methylimidazole and the combination thereof, with or without solvent such as dimethylformamide, dimethylsulfoxide, ethylene glycol, diethylene glycol, acetonitrile, acetone, methyl imidazoles, ionic liquid, water and the like. The reaction time vary from 1 min-12 hrs and yield of the products from 49-76% depending upon the base, acid, substrate source of heating monomode or multimode microwave or conventional. It is important to mention that the presence of 2- or 4-hydroxy substitution at phenyl ring of cinnamic acids and their derivatives is essential requirements towards formation of corresponding arylethenes in one step.

  这项名为“微波诱导的一锅法制备芳基乙烯”的发明提供了一种制备商业上重要的2-或4-羟基取代芳基乙烯（如苯乙烯或苯乙烯）的方法，利用更便宜的底物（2-或4-羟基取代肉桂酸及其衍生物）和碱性试剂（如氢氧化钠、氢氧化钾、氢氧化锂、碳酸氢钠、碳酸钠、碳酸氢钾、碳酸钾、乙酸铵、咪唑、甲基咪唑及其组合物）在一锅中制备。可以使用溶剂（如二甲基甲酰胺、二甲基亚砜、乙二醇、二乙二醇、乙腈、丙酮、甲基咪唑、离子液体、水等），反应时间从1分钟到12小时不等，产物收率为49-76％，具体取决于碱性试剂、酸性试剂、底物、加热方式（单模或多模微波或传统方式）。值得一提的是，肉桂酸及其衍生物苯环上的2-或4-羟基取代是形成相应芳基乙烯的必要条件。
• WO2007/110881
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.