3-(4-hydroxyphenyl)-2-methylacrylic 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: 3-(4-hydroxyphenyl)-2-methylacrylic acid
• 英文别名: α-methyl-p-coumaric acid；3-(4-Hydroxyphenyl)methylacrylate；4-Hydroxy-alpha-methylcinnamic acid；3-(4-hydroxyphenyl)-2-methylprop-2-enoic acid
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: YNMMLKQHOGURNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-2-methylacrylic acid 在 cucumber juice 作用下， 反应 24.0h， 以15%的产率得到4-[(1E)-1-丙烯-1-基]苯酚
  参考文献：
  名称：

  CSJ成为有机转化的通用高效绿色资源†

  摘要：

  已开发出一种简单，新颖，绿色且有效的替代方案，用于将芳族醛还原为相应的醇，将取代的苯甲酸（C 6 -C 1）和取代的肉桂酸（C 6 -C 3）脱羧。通过使用天然原料黄瓜汁（CSJ）（相对绿色的溶剂系统），在相对于酸的对位的羟基上分别形成相应的酚类化合物和乙烯基苯酚，进行底物选择性反应。另外，已经进行了芳族化合物的乙酰基以及苯甲酰基的水解，以通过CSJ提供优异的产率。

  DOI：

  10.1039/c6ra01760f
• 作为产物：
  描述：

  4-[(叔-丁基二甲基甲硅烷)氧代]苯甲醛 在 氢氧化钾 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 8.0h， 生成 3-(4-hydroxyphenyl)-2-methylacrylic acid
  参考文献：
  名称：

  Analogue Chromophore Study of the Influence of Electronic Perturbation on Color Regulation of Photoactive Yellow Protein†

  摘要：

  We report a unique lambda(max) shift of the absorption maximum of a photoactive yellow protein (PYP) analogue reconstituted with a fluorinated chromophore (F-PYP). The difference in lambda(max), between the free chromophore and the protein was significantly larger than that with the native chromophore. We concluded that the unusual,lambda(max) shift is caused by the electronegative character of the fluorine atom and not by steric hindrance. This result suggests that formation of a hydrogen bond between the fluorine atom and one or more amino acid residues could neutralize its electron-withdrawing character. The properties of analogues of PYP with brominated and methylated chromophore could be explained as an effect of steric hindrance.

  DOI：

  10.1562/2006-01-17-ra-781

文献信息

• Synthesis, Characterization and Antitumor Potential of Cinnamoyl Urea Derivatives
  作者：Rakhi Chaudhary、Mohd. Shuaib、S. Riaz Hashim、Prem Shankar Mishra

  DOI：10.14233/ajchem.2016.19403

  日期：——

  Cinnamoyl ureas have been identified as novel compounds with their various biological activities. Some novel cinnamoyl ureas were synthesized successfully by these substitutions, at the phenyl ring, at a,b-unsaturated carbon and the substitution at the carbonyl functionality, which further were studied for their antitumor activity. Thus in this research work, we aimed to use all these active moieties with phenyl urea substitutions at carbonyl moiety. Molecular docking study was used for confirming their interaction with tubulin protein for their antitumor activity. Through in silico molecular docking study, the result showed that all the synthesized compounds (3a-3e) have minimum binding energy and good affinity toward their active pocket, thus they were considered as good antitumor agents.

  肉桂酰脲已被识别为具有多种生物活性的 новél 化合物。通过在苯环、α,β-不饱和碳和羰基功能团的位点进行这些取代，成功合成了一些新型肉桂酰脲，随后研究了它们的抗肿瘤活性。因此，在本研究中，我们旨在利用这些活性基团，并在羰基部分进行苯脲取代。通过分子对接研究，确认了它们与微管蛋白的相互作用以评估抗肿瘤活性。通过计算机分子对接研究，结果显示所有合成的化合物（3a-3e）具有较低的结合能和良好的活性位点亲和力，因此被认为是良好的抗肿瘤剂。
• [EN] NOVEL ALBICIDIN DERIVATIVES, THEIR USE AND SYNTHESIS<br/>[FR] NOUVEAUX DÉRIVÉS D'ALBICIDINE, LEUR UTILISATION ET LEUR SYNTHÈSE
  申请人：UNIV BERLIN TECH

  公开号：WO2022063827A1

  公开（公告）日：2022-03-31

  The present invention relates to an albidicin derivatives, in particular to amid bond isosteres compound according to general formula (1) and (2).

  本发明涉及一种白素霉素衍生物，特别是一种根据通用式（1）和（2）的酰胺键异构化合物。
• Alpha-methylcinnamic acid ester derivative and liquid crystal composition
  申请人：Mitsubishi Rayon Company Ltd.

  公开号：US04751018A1

  公开（公告）日：1988-06-14

  Disclosed is an .alpha.-methylcinnamic acid ester derivative represented by the formula: ##STR1## wherein n is an integer of from 5 to 18, R.sub.1 represents an optically active group of the formula ##STR2## in which m is an integer of from 1 to 5 and *C represents an asymmetric carbon atom, and R.sub.2 represents ##STR3## The .alpha.-methylcinnamic acid ester derivative is valuable as a ferroelectric liquid crystal or an additive to a ferroelectric liquid crystal.

  本发明涉及一种α-甲基肉桂酸酯衍生物，其表示为以下公式：##STR1## 其中n为5至18的整数，R1表示具有以下公式的手性活性基团：##STR2## 其中m为1至5的整数，*C表示不对称碳原子，R2表示##STR3## 该α-甲基肉桂酸酯衍生物可作为铁电液晶或铁电液晶的添加剂具有价值。
• Phenylcarboxylic acid derivatives
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：US04999378A1

  公开（公告）日：1991-03-12

  Phenylcarboxylic acid derivatives having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, --O--D--R.sup.5 (D is alkylene, R.sup.5 is H, amino, morpholino, carboxyl, phthalimido, phenyl, epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl, or both form alkylenedioxy; R.sup.3 is H, --E--R.sup.6 (E is alkylene, R.sup.6 is H, carboxyl, cyano, OH, phenylalkoxy, or halogen-substituted phenyl, or phenylcarbamoyl), --CO--G--R.sup.7 (G is alkylene, R.sup.7 is H, substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl, or halophenyl; R.sup.4 is H or alkyl; A is alkylene, alkylene condensed with cycloalkyl ring, or alkenylene; B is alkylene or alkenylene; l is 0 or 1. Said compounds have fatty acid synthesis-inhibitory activity, cholesterol synthesis-inhibitory activity and are useful as antilipidemic agent, prophylactic and treating agent of artherosclerosis, prophylactic and treating agent of obesity, antidiabetics.

  具有以下式子的苯基羧酸衍生物：##STR1## 其中R.sup.1和R.sup.2分别为H，卤素，烷基，卤代烷基，烷酰基，环烷基，硝基，氨基，--O--D--R.sup.5（D为烷基，R.sup.5为H，氨基，吗啉基，羧基，邻苯二甲酰亚胺，苯基，环氧基），取代或未取代的苯氧基，取代或未取代的苯基烷基氨基，羧基烯基，或两者形成烷基二氧基; R.sup.3为H，--E--R.sup.6（E为烷基，R.sup.6为H，羧基，氰基，OH，苯基烷氧基，或卤代苯基，或苯基氨基酰基），--CO--G--R.sup.7（G为烷基，R.sup.7为H，取代或未取代的苯基氨基酰基），取代或未取代的苯甲酰基，烯基，氨基甲酰基，苯基，或卤代苯基; R.sup.4为H或烷基; A为烷基，烷基与环烷基环缩，或烯基; B为烷基或烯基; l为0或1。这些化合物具有脂肪酸合成抑制活性，胆固醇合成抑制活性，并且可用作抗脂质血症药物，动脉粥样硬化预防和治疗剂，肥胖症预防和治疗剂，抗糖尿病药物。
• CSJ acting as a versatile highly efficient greener resource for organic transformations
  作者：Himadri Sekhar Maity、Kaushik Misra、Tanushree Mahata、Ahindra Nag

  DOI：10.1039/c6ra01760f

  日期：——

  existing protocols have been developed for the reduction of aromatic aldehydes to their corresponding alcohols, decarboxylation of substituted benzoic acids (C6–C1) and substituted cinnamic acids (C6–C3) with a hydroxyl group at the para position with respect to the acid group to corresponding phenolic compounds and vinyl phenols respectively by using a natural feedstock, cucumber juice (CSJ), which

  已开发出一种简单，新颖，绿色且有效的替代方案，用于将芳族醛还原为相应的醇，将取代的苯甲酸（C 6 -C 1）和取代的肉桂酸（C 6 -C 3）脱羧。通过使用天然原料黄瓜汁（CSJ）（相对绿色的溶剂系统），在相对于酸的对位的羟基上分别形成相应的酚类化合物和乙烯基苯酚，进行底物选择性反应。另外，已经进行了芳族化合物的乙酰基以及苯甲酰基的水解，以通过CSJ提供优异的产率。