cis-o-Chlor-zimtsaeure | 704-96-1

• 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: cis-o-Chlor-zimtsaeure
• 英文别名: 2-Chloro-cis-cinnamic acid；(Z)-3-(2-chlorophenyl)prop-2-enoic acid
• CAS: 704-96-1
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: KJRRTHHNKJBVBO-WAYWQWQTSA-N

物化性质

• 熔点：
  127 °C(Solv: ethanol (64-17-5))
• 沸点：
  321.6±17.0 °C(Predicted)
• 密度：
  1.332±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

反应信息

• 作为反应物：
  描述：

  cis-o-Chlor-zimtsaeure 在 溴 作用下， 生成 (E)-邻氯肉桂酸
  参考文献：
  名称：

  Stoermer, Chemische Berichte, 1911, vol. 44, p. 644

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl cis-o-chlorocinnamate 在 sodium hydroxide 作用下， 反应 0.33h， 生成 cis-o-Chlor-zimtsaeure
  参考文献：
  名称：

  Photocyclization of Ortho-Substituted Cinnamic Acids

  摘要：

  Mono and di (i.e. 2, 6) o-chloro- and o-methoxycinnamic acids undergo photocyclization to give the corresponding coumarins. The reaction occurs in aqueous and organic media, with a prototypical reaction giving evidence of being favored at pH > 6. Cyclization of the dimethoxy acid is relatively inefficient (Phi for the PSS = 0.0015), and a photostationary state of the cis/trans acids is formed early into the reaction, The photocyclization of the dichloro analog is more efficient (Phi exceeds 0.04) and therefore time dependent since product formation competes with trans/cis isomerization. Methyl o-chlorocinnamate also photocyclizes (Phi for the PSS = 0.0022 in acetonitrile) but the o-methoxy ester is virtually photoinert, It is proposed that the acid photocyclizes through intramolecular nucleophilic attack by the carboxylate group followed by heterolysis of the nucleofuge. Methyl o-chlorocinnamate appears to photocyclize through a [4 + 2] cycloaddition of the carbonyl group followed by homolysis of the Cl and Me moieties, possibly through the intermediacy of a ketene as proposed by earlier workers.

  DOI：

  10.1021/jo00112a018

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。
• Novel Herbicide Resistance Genes
  申请人：Lira Justin M.

  公开号：US20100251432A1

  公开（公告）日：2010-09-30

  The subject invention provides novel plants that are not only resistant to 2,4-D, but also to a pyridyloxyacetate herbicide. The subject invention also includes plants that produce one or more enzymes of the subject invention “stacked” together with one or more other herbicide resistance genes. The subject invention enables novel combinations of herbicides to be used in new ways. Furthermore, the subject invention provides novel methods of preventing the development of, and controlling, strains of weeds that are resistant to one or more herbicides such as glyphosate. The preferred enzyme and gene for use according to the subject invention are referred to herein as AAD-13 (AryloxyAlkanoate Dioxygenase). This highly novel discovery is the basis of significant herbicide tolerant crop trait and selectable marker opportunities.

  该发明提供了一种新型植物，不仅对2,4-D具有抗性，而且对吡啶氧基乙酸类除草剂也具有抗性。该发明还包括将该发明的一种或多种酶与一种或多种其他除草剂抗性基因“堆叠”在一起的植物。该发明使得新型除草剂的组合可以以新的方式使用。此外，该发明提供了一种防止发展和控制对一种或多种除草剂（如草甘膦）具有抗性的杂草品系的新方法。该发明中用于使用的首选酶和基因被称为AAD-13（芳氧基烷酸双加氧酶）。这一高度新颖的发现是重要的除草剂耐受性作物性状和可选择标记机会的基础。
• USES AND DETECTION OF HERBICIDE RESISTANCE GENES FOR RESISTANCE TO ARYLOXYALKANOATE HERBICIDES
  申请人：Dow AgroSciences LLC

  公开号：US20130040815A1

  公开（公告）日：2013-02-14

  The subject invention provides novel plants that are not only resistant to 2,4-D, but also to a pyridyloxyacetate herbicide. The subject invention also includes plants that produce one or more enzymes of the subject invention “stacked” together with one or more other herbicide resistance genes. The subject invention enables novel combinations of herbicides to be used in new ways. Furthermore, the subject invention provides novel methods of preventing the development of, and controlling, strains of weeds that are resistant to one or more herbicides such as glyphosate. The preferred enzyme and gene for use according to the subject invention are referred to herein as AAD-13 (AryloxyAlkanoate Dioxygenase). This highly novel discovery is the basis of significant herbicide tolerant crop trait and selectable marker opportunities.

  本发明提供了新型植物，不仅对2,4-D具有抗性，还对吡啶氧乙酸类除草剂具有抗性。本发明还包括将本发明的一种或多种酶“叠加”在一起与一种或多种其他除草剂抗性基因一起产生的植物。本发明使得新型除草剂的组合可以以新的方式使用。此外，本发明提供了预防和控制对一种或多种除草剂如草甘膦具有抗性的杂草株的新方法。本发明中用于使用的首选酶和基因被称为AAD-13（芳氧基烷酸双加氧酶）。这一高度新颖的发现是显著的除草剂耐受农作物特征和可选择标记机会的基础。
• 反式和顺式α,β不饱和羧酸的合成方法
  申请人：南方科技大学

  公开号：CN117700315A

  公开（公告）日：2024-03-15

  反式和顺式α,β不饱和羧酸的合成方法，涉及有机合成技术领域，其包括以烯基卤代物(I)和甲酸盐为原料，加入镍催化剂、光催化剂、联吡啶类配体和有机溶剂，在惰性气氛中，在蓝光照射下，室温下搅拌至反应完毕。本发明的方法反应条件温和，不需要氧化剂以及高温条件，同时避免了过渡金属的残留，从稳定易制备的各种烯基卤代物直接得到反式或顺式α,β不饱和羧酸化合物。
• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  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.