(Z)-3-(4-bromophenyl)acrylic acid | 5676-63-1

• 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)-3-(4-bromophenyl)acrylic acid
• 英文别名: Z-4-bromocinnamic acid；cis-p-Brom-zimtsaeure；(Z)-3-(4-bromophenyl)prop-2-enoic acid
• CAS: 5676-63-1
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: CPDDDTNAMBSPRN-UTCJRWHESA-N

物化性质

• 沸点：
  344.9±17.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-bromophenyl)acrylic acid 在 吡啶 、 氯化亚砜 作用下， 反应 0.5h， 以71%的产率得到3-氯-6-溴-2-苯并噻吩甲酰氯
  参考文献：
  名称：

  Ried, Walter; Oremek, Gerhard; Ocakcioglu, Belkis, Liebigs Annalen der Chemie, 1980, # 9, p. 1424 - 1427

  摘要：

  DOI：
• 作为产物：
  描述：

  对溴苯甲醛 在 水 、 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 (Z)-3-(4-bromophenyl)acrylic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• A linear solvation energy relationship study for the reactivity of 2-(4-substituted phenyl)-cyclohex-1-enecarboxylic, 2-(4-substituted phenyl)-benzoic, and 2-(4-substituted phenyl)-acrylic acids with diazodiphenylmethane in various solvents
  作者：J. B. Nikolić、G. S. Ušćumlić、I. O. Juranić

  DOI：10.1002/kin.20497

  日期：2010.7

  were carried out by means of multiple linear regression analysis, and the solvent effects on the reaction rates were analyzed in terms of initial and transition state contributions. The signs of the equation coefficients support the proposed reaction mechanism. The solvation models for all investigated carboxylic acids are suggested. The quantitative relationship between the molecular structure and the

  研究了2-（4-取代苯基）-环己-1-烯酸，2-（4-取代苯基）-苯甲酸和2-（4-取代苯基）丙烯酸与重氮二苯甲烷在各种溶剂中的反应性。为了解释通过溶剂效应产生的动力学结果，使用卡姆莱特-塔夫脱（Kamlet-Taft）溶剂变色方程将所检查酸的二级速率常数进行了关联。通过多元线性回归分析进行动力学数据的相关性，并根据初始和过渡态贡献分析了溶剂对反应速率的影响。方程系数的符号支持所提出的反应机理。建议了所有研究的羧酸的溶剂化模型。讨论了分子结构与化学反应性之间的定量关系，以及几何形状对所检查分子的反应性的影响。©2010 Wiley Periodicals，Inc.国际化学杂志Kinet 42：430–439，2010
• Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of Z-cinnamic acid derivatives†
  作者：Rocío B. Rodríguez、Ramiro L. Zapata、María L. Salum、Rosa Erra-Balsells

  DOI：10.1039/d0pp00072h

  日期：2020.6

  Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also

  研究了MeCN中一系列取代的E-肉桂酸的酸形式及其相应的质子离子液体（PIL）在300 nm的光下的光异构化。研究了取代基的性质，强度，数量和位置对E-肉桂酸酯衍生物光化学行为的影响。还研究了在米氏酮存在下该反应的光敏化在366 nm的情况，这表明反应中涉及三重激发态。由于n的存在在所有情况下，形成PIL所需的丁胺都会显着提高光产物的产率，并讨论了PIL的作用。因此，对这些基本方面的理解已经使我们能够建立成功地合成Z-肉桂酸的优异且实用的合成方案。
• Isoquinolines as urokinase inhibitors
  申请人：Pfizer Inc.

  公开号：US06248738B1

  公开（公告）日：2001-06-19

  Compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein one of R1 and R2 is H and the other is N═C(NH2)2 or NHC(═NH)NH2, and the other substituents are as defined herein, are urokinase (uPA) inhibitors.

  式(I)的化合物及其药学上可接受的盐，其中R1和R2中的一个是氢，另一个是N═C(NH2)2或NHC(═NH)NH2，其他取代基如本文所定义，是尿激酶（uPA）抑制剂。
• MATRIX METALLOPROTEINASE INHIBITORS
  申请人：Ranbaxy Laboratories Limited

  公开号：EP2074093A2

  公开（公告）日：2009-07-01
• [EN] MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA MÉTALLOPROTÉINASE MATRICIELLE
  申请人：RANBAXY LAB LTD

  公开号：WO2008023336A2

  公开（公告）日：2008-02-28

  [EN] The present invention relates to ß-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure ß-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over- activation of a matrix metalloproteinase using the compounds.
  [FR] La présente invention concerne des acides carboxyliques à substitution ß-hydroxy et amino qui agissent en tant qu'inhibiteurs de la métalloprotéase matricielle, en particulier des acides ß-hydroxy carboxyliques purs sur le plan diastéréomérique. L'invention concerne également les procédés correspondants de synthèse des composés de la présente invention et des compositions pharmaceutiques contenant lesdits composés. Les composés de la présente invention sont utilisables pour le traitement de diverses maladies inflammatoires, auto-immunes et allergiques, telles que l'asthme, la polyarthrite rhumatoïde, la bronchopneumopathie chronique obstructive (Chronic Obstructive Pulmonary Disease : COPD), la rhinite, l'arthrose, le psoriasis arthropathique, le psoriasis, la fibrose pulmonaire, les retards de cicatrisation, l'inflammation pulmonaire, le syndrome de détresse respiratoire aiguë, la parodontite, la sclérose en plaques, la gingivite, l'athérosclérose, la prolifération néointimale qui conduit à la resténose et à l'insuffisance cardiaque ischémique, les attaques, les maladies rénales, la métastase tumorale et d'autres affections inflammatoires caractérisées par la sur-expression et la sur-activation d'une métalloprotéase matricielle, à l'aide des composés.