2-hydroxy-4-oxo-4-(4-chlorophenyl)-2-butenoic acid | 149281-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-4-oxo-4-(4-chlorophenyl)-2-butenoic acid
• 英文别名: 2-hydroxy-4-(4'-chlorophenyl)-4-oxo-2-butenoic acid
• CAS: 149281-55-0
• 化学式: C₁₀H₇ClO₄
• 分子量: 226.616
• InChiKey: KGKACLSPOFDTAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-oxo-4-(4-chlorophenyl)-2-butenoic acid 在 丙酸酐 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 N'-[5-(4-chlorophenyl)-2-oxofuran-3(2H)-ylidene]-furan-2-carbohydrazide
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-arylamides of 4-aryl- and 4-(thiophen-2-yl)-2-[2-(furan-2-carbonyl)hydrazono]-4-oxobutanoic acids

  摘要：

  DOI：

  10.1007/s11172-023-4021-9

文献信息

• Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and <i>o</i>-aminothiophenol
  作者：Ekaterina E Stepanova、Maksim V Dmitriev、Andrey N Maslivets

  DOI：10.3762/bjoc.16.193

  日期：——

  Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out.

  通过呋喃-2,3-二酮或酰基丙酮酸在碳化二亚胺存在下与邻氨基苯硫酚的反应，我们开发了两种合成融合了 1,4-苯并噻嗪-2-酮分子的烯酰胺酮的方法，这些烯酰胺酮在生物活性、化学传感器和荧光研究方面具有重要意义。目标烯酮与具有药学意义的 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮一起形成。通过呋喃-2,3-二酮与邻氨基苯硫酚的溶剂切换反应，开发了一种 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮的选择性合成方法。对新化合物进行了初步的生物检测（抗菌、急性毒性）。
• Iminofurans chemistry: IV. Synthesis and structure of 2-N-aryl-substituted derivatives of 2-amino-4-aryl-4-oxobut-2-enoic and 2-amino-5,5-dimethyl-4-oxohex-2-enoic acids
  作者：N. M. Igidov、A. E. Rubtsov、A. V. Tyuneva、V. V. Zalesov、A. Yu. Borodin、E. V. Bukanova

  DOI：10.1134/s1070428009050091

  日期：2009.5

  Reactions of arylamines with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic acids gave rise to 4-aryl-2-arylamino-4-oxobut-2-enoic and 2-aryl-amino-5,5-dimethyl-4-oxohex-2-enoic acids that existed in solutions as Z- and E-isomers or in a ring form as 3-arylamino-5-tert-butyl-5-hydroxyfuran-2(5H)-ones. The probable cyclization mechanism of these compounds into 5-R-3-a

  芳基胺与4-芳基-2-羟基-4-氧代丁-2-烯酸和2-羟基-5,5-二甲基-4-氧己基-2-烯酸的反应产生了4-芳基-2-芳基氨基-4 -Oxobut-2-enoic和2-芳基-氨基-5,5-二甲基-4-Oxohex-2-enoic酸在溶液中以Z-和E-异构体形式存在或以环形式以3-芳基氨基-5-形式存在叔丁基-5-羟基呋喃-2（5H）-ones。考虑了这些化合物可能的环化成5-R-3-arylimino-3 H-呋喃-2-酮衍生物的机理。
• Chemistry of iminofurans: XI. Synthesis, structure, and cyclization of 4-substituted 2-(aroylhydrazinylidene)-4-oxobutanoic acids
  作者：N. M. Igidov、M. A. Kiselev、A. E. Rubtsov

  DOI：10.1134/s1070428016040084

  日期：2016.4

  Aromatic hydrazides reacted with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl- 4-oxohex-2-enoic acids to give 4-aryl-2-(2-aroylhydrazinylidene)-4-oxobutanoic and 5,5-dimethyl-2-(aroylhydrazinylidene)- 4-oxohexanoic acids. The products were found to exist in solution as mixtures of Z/E-hydrazinylidene and cyclic dihydropyrazole tautomers, and they underwent intramolecular cyclization

  芳族酰肼与4-芳基-2-羟基-4-氧代丁-2-烯酸和2-羟基-5,5-二甲基-4-氧己基-2-烯酸反应生成4-芳基-2-（2-芳酰基肼基亚烷基）-4-氧代丁酸和5,5-二甲基-2-（芳酰基肼基亚烷基）-4-氧代己酸。发现产物以Z / E-肼基亚甲基和环状二氢吡唑互变异构体的混合物的形式存在于溶液中，并且它们经过分子内环化成5-芳基5-叔丁基-3-（芳酰基肼基亚基）呋喃-2（3 H）-ones在乙酸酐的作用下。
• Polarographic behavior of 4-aryl-2-(1,2-diphenyl-2-oxoethylidenehydrazino)-4-oxo-2-butenoic acids
  作者：G. S. Posyagin、M. A. Vikhareva、O. A. Bystritskaya、A. E. Rubtsov、P. G. Neifeld、V. V. Zalesov

  DOI：10.1134/s1070363209110140

  日期：2009.11

  Polarographic reduction of 4-aryl-2-(1,2-diphenyl-2-oxoethylidenehydrazino)-4-oxo-2-butenoic acids in 2-propanol-water solutions proceeds with the formation of two or three irreversible cathode waves and leads to 4-aryl-2-(1,2-diphenyl-2-hydroxyethylhydrazino)-4-hydroxybutanoic acids. The latter suffer hydrolysis with the rupture of the C2-NH bond and the formation of 4-aryl-2,4-dihydroxybutanoic acids

  极谱还原2-丙醇水溶液中的4-芳基-2-（1,2-二苯基-2-氧亚乙基肼基肼基）-4-氧代-2-丁烯酸的极谱还原反应会形成两个或三个不可逆的阴极波，并导致4-芳基-2-（1,2-二苯基-2-羟基乙基肼基）-4-羟基丁酸。后者由于C 2 -NH键的断裂和4-芳基-2，4-二羟基丁酸的形成而水解。
• Chemistry of Iminofuran: XVI. Synthesis, Structure, Biological Activity, and Cyclization of 4-Oxo-2-(2-phenylaminobenzoylhydrazono)butanoic Acids
  作者：I. A. Kizimovaa、N. M. Igidov、S. V. Chaschina、I. N. Chernov、A. E. Rubtsov

  DOI：10.1134/s1070428019110101

  日期：2019.11

  The reaction of (2-phenylaminobenzoyl)hydrazine with 4-aryl-2-hydroxy-4-oxobut-2-enoic and 2-hydroxy-5,5-dimethyl-4-oxohex-2-enoic acids results in the formation of 4-aryl-2-(2-phenylaminobenzoyl-hydrazono)-4-oxobutanoic and 5,5-dimethyl-2-(2-phenylaminobenzoylhydrazono)-4-oxohexanoic acids. The products in solutions are present as mixtures of a Z,E-hydrazono form and a cyclic pyrazolinic form, and

  （2-苯基氨基苯甲酰基）肼与4-芳基-2-羟基-4-氧代丁烯2-烯酸和2-羟基-5,5-二甲基-4-氧杂-2-烯酸的反应导致生成4 -芳基-2-（2-苯基氨基苯甲酰肼基）-4-氧代丁酸和5,5-二甲基-2-（2-苯基氨基苯甲酰肼基）-4-氧己酸。溶液中的产物以Z，E-肼基和环状吡唑啉的混合物形式存在，在乙酸酐的作用下，它们在5-芳基和5-叔丁基-3-（2-苯基氨基苯甲酰肼）中环化。 -呋喃-2,3-二酮。测试了4-芳基-2-（2-苯基氨基苯甲酰肼基）-4-氧代丁酸和5,5-二甲基-2-（2-苯基氨基苯甲酰肼基）-4-氧己酸的抗伤害性和抗炎活性。