cis-2,6-Dichlorocinnamic acid | 20595-50-0

• 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-2,6-Dichlorocinnamic acid
• 英文别名: 2,6-dichloro-cis-cinnamic acid；2,6-Dichlor-cis-zimtsaeure；(Z)-3-(2,6-Dichlorophenyl)propenoic acid；(Z)-3-(2,6-dichlorophenyl)prop-2-enoic acid
• CAS: 20595-50-0
• 化学式: C₉H₆Cl₂O₂
• 分子量: 217.051
• InChiKey: OIPVGRCXMFBNAN-PLNGDYQASA-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：
  0.0
• 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-2,6-Dichlorocinnamic acid 生成 5-chlorocoumarin
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 cis-2,6-Dichlorocinnamic acid
  参考文献：
  名称：

  Lindenfors, Arkiv foer Kemi, 1959, vol. 14, p. 227,229

  摘要：

  DOI：

文献信息

• Studies on plant growth-regulating substances XXV. The plant growth-regulating activity of cinnamic acids
  作者：E. N. UGOCHUKWU、R. L. WAIN

  DOI：10.1111/j.1744-7348.1968.tb04515.x

  日期：1968.2

  SUMMARYEffects of ring substitution on the plant growth‐regulating activities of trans‐ and cis‐cinnamic acids have been investigated in the wheat cylinder, pea segment and pea curvature tests. Most of the cis‐ acids were shown to be active. Substitution of fluorine, chlorine or bromine into the ring of cis‐cinnamic acid in most cases increased the activity. The results are discussed in relation to mode of action and chemical structure/biological activity relationships: 4‐chlorobenzoic acid is shown to act as a competitive antagonist towards 4‐chloro‐cis‐cinnamic acid.