(Z)-3-(3-硝基苯基)丙烯酸 | 5676-61-9

• 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
• 中文名称: (Z)-3-(3-硝基苯基)丙烯酸
• 英文名称: cis-m-Nitro-zimtsaeure
• 英文别名: cis-m-Nitrocinnamic acid；(Z)-3-(3-nitrophenyl)prop-2-enoic acid
• CAS: 5676-61-9
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: WWXMVRYHLZMQIG-PLNGDYQASA-N

物化性质

• 熔点：
  179.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3-硝基苯基)丙烯酸 在 lithium acetate 、 1-氯苯并三氮唑 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以87%的产率得到Z-1-(2-chloroethenyl)-3-nitrobenzene
  参考文献：
  名称：

  Katritzky, Alan R.; Majumder, Suman; Jain, Ritu, Journal of the Indian Chemical Society, 2003, vol. 80, # 11, p. 1073 - 1075

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-ethyl 3-(3-nitrophenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到(Z)-3-(3-硝基苯基)丙烯酸
  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

• Control of the Solid-state photodimerization of some derivatives and analogs of trans-cinnamic acid by ethylenediamine
  作者：Yoshikatsu Ito、Bozena Borecka、Gunnar Olovsson、James Trotter、John R Scheffer

  DOI：10.1016/0040-4039(95)01210-9

  日期：1995.8

  Some of double salts derived from ethylenediamine (en) and a variety of trans-cinnamic acids and their analogs underwent photodimerization in the solid state, giving predominantly β-truxinic dimers. X-Ray studies demonstrate that (a) the conformation of en is gauche for the highly photoreactive double salts (o-1b·en and m-1e·en), whereas it is anti for lessphotoreactive o-1a·en or photoinert 1d·en

  某些衍生自乙二胺（en）的复盐和各种反式肉桂酸及其类似物在固态下进行了光二聚，主要产生β-精氨酸二聚体。X射线研究表明（a）对于高光反应性双盐（o- 1b·en和m- 1e·en），en的构象是胶状，而对光反应性较低的o- 1a·en或光惰性1d·是不利的。 en和（b）对于高反应性o- 1b·en和m- 1e·en而言，单体酸分子以重叠构型排列，并且反应性单体对通过氢脱键键合到同一en分子上。
• AMINOPHENYLPROPANOIC ACID DERIVATIVE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1726580A1

  公开（公告）日：2006-11-29

  A compound represented by the formula (1): wherein each symbol is as defined in the specification, and a salt thereof and a prodrug thereof unexpectedly have superior GPR40 receptor agonist activity, superior in the properties as a pharmaceutical product such as stability and the like, and can be a safe and useful pharmaceutical agent as a drug for the prophylaxis or treatment of GPR40 receptor related pathology or diseases such as diabetes and the like.

  式 (1) 所代表的化合物： 其中各符号如说明书中所定义，其盐及其原药意外地具有优异的 GPR40 受体激动剂活性、优异的稳定性等药剂特性，可作为预防或治疗 GPR40 受体相关病理或疾病（如糖尿病等）的安全有用的药剂。
• Ried, Walter; Oremek, Gerhard; Ocakcioglu, Belkis, Liebigs Annalen der Chemie, 1980, # 9, p. 1424 - 1427
  作者：Ried, Walter、Oremek, Gerhard、Ocakcioglu, Belkis

  DOI：——

  日期：——
• Wollring, Chemische Berichte, 1914, vol. 47, p. 114
  作者：Wollring

  DOI：——

  日期：——
• Hadjoudis,E. et al., Journal of the Chemical Society. Perkin transactions II, 1972, p. 1056 - 1060
  作者：Hadjoudis,E. et al.

  DOI：——

  日期：——