(Z)-2-bromo-3-(p-tolyl)propenoic acid | 182884-62-4

• 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: (Z)-2-bromo-3-(p-tolyl)propenoic acid
• 英文别名: (Z)-2-bromo-3-p-tolylacrylic acid；α-bromo-4-methyl-cinnamic acid；α-Brom-4-methyl-zimtsaeure；2-bromo-4'-methyl-cinnamic acid；(Z)-2-bromo-3-(4-methylphenyl)prop-2-enoic acid
• CAS: 182884-62-4
• 化学式: C₁₀H₉BrO₂
• 分子量: 241.084
• InChiKey: VOVRWXAQNUXIFI-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-bromo-3-(p-tolyl)propenoic acid 、 苄脒盐酸盐 在 copper(I) oxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到2-phenyl-4-(4'-methylbenzylidene)-2-imidazolin-5-one
  参考文献：
  名称：

  Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones

  摘要：

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.

  DOI：

  10.1021/ol1008813
• 作为产物：
  描述：

  Ethyl 2-bromo-3-(4-methylphenyl)prop-2-enoate 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以82%的产率得到(Z)-2-bromo-3-(p-tolyl)propenoic acid
  参考文献：
  名称：

  Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones

  摘要：

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.

  DOI：

  10.1021/ol1008813

文献信息

• Chemical fixation of carbon dioxide by copper catalyzed multicomponent reactions for oxazolidinedione syntheses
  作者：Siddharth Sharma、Ajay K. Singh、Devendra Singh、Dong-Pyo Kim

  DOI：10.1039/c4gc02089h

  日期：——

  The quest to reduce greenhouse gases has triggered the development of new chemical fixation of carbon dioxide.

  减少温室气体排放的探索已经引发了新的化学固定二氧化碳的发展。
• Cu/Cu_xO_y NPs architectured COF: a recyclable catalyst for the synthesis of oxazolidinedione <i>via</i> atmospheric cyclizative CO₂ utilization
  作者：Somnath Sarkar、Swarbhanu Ghosh、Jahangir Mondal、Sk. Manirul Islam

  DOI：10.1039/d0cc04835f

  日期：——

  organic skeletons. In the presence of a catalytic Cu/CuxOy NP-loaded COF, several 2-bromo-3-alkylacrylic acids combined with several amine derivatives and CO2 (0.1 MPa) are converted to the desired oxazolidinediones in excellent yields (up to 96%) under alkali-free conditions and ambient temperature.

  本研究描述了具有优异的表面积，可调节的孔径和巨大的CO 2捕集效率的结晶共价有机骨架（COF）的有利构造，可通过将CO 2引入反应性极强的有机骨架中来促进新型多组分环化。在催化性Cu / Cu x O y NP负载的COF的存在下，几种2-溴-3-烷基丙烯酸与几种胺衍生物和CO 2（0.1 MPa）的结合以优异的收率转化为所需的恶唑烷二酮。 96％）在无碱条件和环境温度下进行。
• Gattermann, Justus Liebigs Annalen der Chemie, 1906, vol. 347, p. 353
  作者：Gattermann

  DOI：——

  日期：——
• Addition Reactions of Unsaturated Alpha-Ketonic Acids. V
  作者：Marie Reimer、Elizabeth Chase

  DOI：10.1021/ja01277a051

  日期：1938.10
• Hamed, E. A.; Sharaf, S. M.; El-Hegazy, Fatma M., Egyptian Journal of Chemistry, 1996, vol. 39, # 5, p. 455 - 464
  作者：Hamed, E. A.、Sharaf, S. M.、El-Hegazy, Fatma M.、Youssef, A. A.

  DOI：——

  日期：——