2-(4-methoxy-phenyl)-3-phenyl-acrylic acid | 6387-65-1

• 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: 2-(4-methoxy-phenyl)-3-phenyl-acrylic acid
• 英文别名: β-Phenyl-α-(4-methoxy-phenyl)-acrylsaeure；2-(4-Methoxy-phenyl)-3-phenyl-acrylsaeure；4-Methoxy-stilben-α-carbonsaeure；α-(4-Methoxy-phenyl)-zimtsaeure；α--zimtsaeure；2-(4-Methoxyphenyl)-3-phenylprop-2-enoic acid
• CAS: 6387-65-1
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: IXCMHNHRDGRKDS-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C
• 沸点：
  386.9±27.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 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-(4-methoxy-phenyl)-3-phenyl-acrylic acid 在 phosphorous (V) sulfide 、 sulfur 作用下， 生成 4-(4-methoxy-phenyl)-5-phenyl-[1,2]dithiol-3-thione
  参考文献：
  名称：

  Jirousek; Starka, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1982,1984, 1985

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-2-(4-甲氧基-苯基)-3-苯基-丙酸 在 sodium acetate 、 乙酸酐 作用下， 生成 2-(4-methoxy-phenyl)-3-phenyl-acrylic acid
  参考文献：
  名称：

  Joerlander, Chemische Berichte, 1917, vol. 50, p. 417

  摘要：

  DOI：

文献信息

• Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent
  作者：Jinhe Lv、Lingbo Zong、Jinrong Zhang、Jiaxin Song、Jinyu Zhao、Kai Zhang、Ziqin Zhou、Mingjie Gao、Congxia Xie、Xiaofei Jia、Xinyi Ren

  DOI：10.1039/d1cy00699a

  日期：——

  β-unsaturated carboxylic acids from alkynes with CO and H2O was described. The atom-economic hydroxycarbonylation of various symmetrical and unsymmetrical alkynes can be achieved with chemo-, stereo-, and regioselectivity, affording the corresponding carboxylic acids in good to excellent yields. Using water as the reaction solvent, the water-soluble palladium catalyst was easily separated from the product and

  描述了亚砜磷改性的钯催化从炔烃与 CO 和 H 2 O合成 α,β-不饱和羧酸。各种对称和不对称炔烃的原子经济羟基羰基化可以通过化学选择性、立体选择性和区域选择性实现，从而以良好到优异的产率提供相应的羧酸。以水为反应溶剂，水溶性钯催化剂容易与产物分离，可重复使用5次。
• Synthesis of Vinyl Carboxylic Acids using Carbon Dioxide as a Carbon Source by Iron-Catalyzed Hydromagnesiation
  作者：Rajagopal Santhoshkumar、Ya-Chun Hong、Ching-Zong Luo、Yun-Ching Wu、Chen-Hsun Hung、Kuen-Yuan Hwang、An-Pang Tu、Chien-Hong Cheng

  DOI：10.1002/cctc.201600279

  日期：2016.7.6

  iron‐catalyzed synthesis of α,β‐unsaturated carboxylic acids from alkynes and carbon dioxide was developed. This reaction proceeds through hydromagnesiation of alkynes followed by carbon dioxide insertion under atmospheric pressure and ambient temperature in the presence of iron and a Grignard reagent as a catalyst and hydride source, respectively. Several symmetrical and unsymmetrical alkynes were transformed

  开发了由炔烃和二氧化碳铁催化的α，β-不饱和羧酸的合成方法。该反应通过炔烃的加氢放大进行，然后在大气压和环境温度下分别在铁和格氏试剂作为催化剂和氢化物源的存在下插入二氧化碳。几种对称和不对称炔烃以良好或优异的收率转化为相应的酸。该方法提供了合成乙烯基羧酸的有效途径。
• A convenient way to dibenzo[c,h]-1,5-naphthyridines (11-aza-benzo[c] phenanthridines)
  作者：Emile Bisagni、Corinne Landras、Sylvie Thirot、Christiane Huel

  DOI：10.1016/0040-4020(96)00579-0

  日期：1996.7

  Whereas thermal cyclisation of variously substituted 2,3-diarylacrylazides easily provided a new way to 3-aryl-isoquinolones, nitration of these compounds mainly led to corresponding 3-aryl-4-nitro-isoquinolones. After reduction into 4-amino-3-aryl-isoquinolones, amidification and subsequent cyclization gave the yet unknown title compounds.

  尽管各种取代的2，3-二芳基丙烯酰胺的热环化很容易为3-芳基-异喹诺酮提供了新的途径，但这些化合物的硝化作用主要产生了相应的3-芳基-4-硝基-异喹诺酮。还原成4-氨基-3-芳基-异喹诺酮后，酰胺化和随后的环化反应产生了未知的标题化合物。
• Discovery of a new chemical series of BRD4(1) inhibitors using protein-ligand docking and structure-guided design
  作者：Bryan C. Duffy、Shuang Liu、Gregory S. Martin、Ruifang Wang、Ming Min Hsia、He Zhao、Cheng Guo、Michael Ellis、John F. Quinn、Olesya A. Kharenko、Karen Norek、Emily M. Gesner、Peter R. Young、Kevin G. McLure、Gregory S. Wagner、Damodharan Lakshminarasimhan、Andre White、Robert K. Suto、Henrik C. Hansen、Douglas B. Kitchen

  DOI：10.1016/j.bmcl.2015.04.107

  日期：2015.7

  Bromodomains are key transcriptional regulators that are thought to be druggable epigenetic targets for cancer, inflammation, diabetes and cardiovascular therapeutics. Of particular importance is the first of two bromodomains in bromodomain containing 4 protein (BRD4(1)). Protein-ligand docking in BRD4(1) was used to purchase a small, focused screening set of compounds possessing a large variety of core structures. Within this set, a small number of weak hits each contained a dihydroquinoxalinone ring system. We purchased other analogs with this ring system and further validated the new hit series and obtained improvement in binding inhibition. Limited exploration by new analog synthesis showed that the binding inhibition in a FRET assay could be improved to the low mu M level making this new core a potential hit-to-lead series. Additionally, the predicted geometries of the initial hit and an improved analog were confirmed by X-ray co-crystallography with BRD4(1). (C) 2015 Elsevier Ltd. All rights reserved.