2-hydroxy-4-oxo-4-(p-tolyl)but-2-enoic acid | 113282-74-9

• 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-(p-tolyl)but-2-enoic acid
• CAS: 113282-74-9
• 化学式: C₁₁H₁₀O₄
• mdl: MFCD24388711
• 分子量: 206.198
• InChiKey: HTHFQYJFCHROLP-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  397.3±42.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 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：
  0.09
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-oxo-4-(p-tolyl)but-2-enoic acid 在 丙酸酐 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成
  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
• 作为产物：
  描述：

  Methyl 3-(4-methylbenzoyl)-4,5-dioxo-1-phenylpyrrole-2-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以79%的产率得到2-hydroxy-4-oxo-4-(p-tolyl)but-2-enoic acid
  参考文献：
  名称：

  Andreichikov, Yu. S.; Maslivets, A. N.; Smirnova, L. I., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1378 - 1387

  摘要：

  DOI：

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。
• Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives
  作者：N. A. Pulina、V. Yu. Kozhukhar、A. S. Kuznetsov、A. E. Rubtsov、A. V. Starkova

  DOI：10.1007/s11172-017-1914-5

  日期：2017.8

  ut-2-ene-1,4-diones and 2-[2-(3-R-adamantan-1-yl)-2-oxoethylidene]hydrazinyl}-4-(het)aryl-4-oxobut-2-enoic acids were synthesized and used to obtain water-soluble compounds. Their influence on the blood coagulation system was studied, which revealed compounds with a high hemostatic activity and a low acute toxicity. A relationship between structure and pharmacological effect of the synthesized compounds

  新的4-芳基-2-(4-芳基氨基)-1-(哌嗪-1-基)丁-2-烯-1,4-二酮和2-[2-(3-R-金刚烷-1-基) )-2-oxoethylidene]hydrazinyl}-4-(het)aryl-4-oxobut-2-enoic 酸被合成并用于获得水溶性化合物。研究了它们对凝血系统的影响，揭示了具有高止血活性和低急性毒性的化合物。建立了合成化合物的结构和药理作用之间的关系。
• 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。