(Z)-methyl 2-hydroxy-4-(4-methylphenyl)-4-oxobut-2-enoate | 39848-01-6

• 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: (Z)-methyl 2-hydroxy-4-(4-methylphenyl)-4-oxobut-2-enoate
• 英文别名: methyl 2-hydroxy-4-(4-methylphenyl)-4-oxo-2-butenoate；p-toluylpyruvic acid methyl ester
• CAS: 39848-01-6
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: NXPWLSZFBIFKLI-XFFZJAGNSA-N

物化性质

• 沸点：
  363.9±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 2-hydroxy-4-(4-methylphenyl)-4-oxobut-2-enoate 在 sodium acetate 、 乙酸酐 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 39.0h， 生成 4,4-Dihydroxy-5-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  Pimenova, E. V.; Andreichikov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 2.2, p. 302 - 315

  摘要：

  DOI：
• 作为产物：
  描述：

  在 acetate buffer solution 、 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 (Z)-methyl 2-hydroxy-4-(4-methylphenyl)-4-oxobut-2-enoate
  参考文献：
  名称：

  Kozlov; Perevozchikov; Kozlova, Russian Journal of Organic Chemistry, 1997, vol. 33, # 3, p. 353 - 358

  摘要：

  DOI：

文献信息

• Synthesis and SAR of 4-Aryl-2-hydroxy-4-oxobut-2-enoic Acids and Esters and 2-Amino-4-aryl-4-oxobut-2-enoic Acids and Esters:  Potent Inhibitors of Kynurenine-3-hydroxylase as Potential Neuroprotective Agents
  作者：Martin J. Drysdale、S. Lucy Hind、Marilyn Jansen、John F. Reinhard

  DOI：10.1021/jm990396t

  日期：2000.1.1

  The synthesis and structure-activity relationship of a series of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2-enoic acids and esters as potent inhibitors of kynurenine-3-hydroxylase are described. These compounds are the most potent inhibitors of the kynurenine-3-hydroxylase enzyme so far disclosed. Additionally methyl 4-(3-chlorophenyl)-2-hydroxy-4-oxobut-2-enoate

  一系列有效的4-芳基-2-羟基-2-羟基-4-氧代丁-2-烯酸和酯与2-氨基-4-芳基-4-氧代丁-2-烯酸和酯的合成及其构效关系描述了犬尿氨酸-3-羟化酶的抑制剂。这些化合物是迄今公开的最有效的犬尿氨酸-3-羟化酶的抑制剂。此外，4-（3-氯苯基）-2-羟基-4-氧代丁-2-烯酸甲酯（2d），4-（3-氯苯基）-2-羟基-4-氧代丁-2-烯酸（3d），甲基4-（3-氟苯基）-2-羟基-4-氧丁-2-烯酸酯（2f）和4-（3-氟苯基）-2-羟基-4-氧丁-2-烯酸（3f）干扰素-γ诱导的人外周血单核细胞衍生巨噬细胞原代培养物中喹啉酸的合成。
• CONJUGATES DERIVED FROM NON-STEROIDAL ANTI-INFLAMMATORY DRUGS AND METHODS OF USE THEREOF IN IMAGING
  申请人：Reiley Pharmaceuticals, Inc.

  公开号：US20150374858A1

  公开（公告）日：2015-12-31

  Conjugates derived from non-steroidal anti-inflammatory drugs (NSAIDs) and methods of use thereof are disclosed, useful for, inter alia, identifying and localizing the site of pathology and/or inflammation responsible for the sensation of pain in a patient; for identifying the sites of primary, secondary, benign, or malignant tumors; and for diagnosing infection or confirming or ruling out suspected infection. The NSAID-based conjugates contain an imaging moiety. The conjugates concentrate at sites of increased cyclooxygenase expression, thus revealing the sites of increased prostaglandin production, which is correlated with pain and inflammation, and correlated with tumor presence and/or location. Identifying areas of increased COX expressing can also aid in screening for infections.

  披露了来自非甾体抗炎药（NSAIDs）的衍生物及其使用方法，这对于识别和定位患者疼痛感觉的病理和/或炎症部位；识别原发、继发、良性或恶性肿瘤的部位；以及诊断感染或确认或排除疑似感染非常有用。基于NSAID的偶联物含有成像基团。这些偶联物在环氧化酶表达增加的部位富集，从而揭示了前列腺素产生增加的部位，这与疼痛和炎症有关，并与肿瘤存在和/或位置有关。识别COX表达增加的区域也有助于筛查感染。
• Asymmetric Organocatalytic Cascade Michael/Hemiketalization/Retro-Aldol Reaction of 2-[(<i>E</i>)-2-Nitrovinyl]phenols with 2,4-Dioxo-4-arylbutanoates: A Convenient Access to Chiral α-Keto Esters
  作者：Yunting Liu、Youming Wang、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/adsc.201300552

  日期：2013.9.16

  unprecedented organocatalytic enantioselective cascade Michael/hemiketalization/retro‐aldol reaction of 2‐[(E)‐2‐nitrovinyl]phenols and 2,4‐dioxo‐4‐arylbutanoates is described. With a bifunctional squaramide catalyst incorporating (1R,2R)‐1,2‐diphenylethane‐1,2‐diamine, the reactions afford products in 75–99% yields with 80–98% ee. This process provides an enantioselective pathway for the synthesis of chiral

  描述了2-[（（E））-2-硝基乙烯基]苯酚与2,4-二氧代-4-芳基丁酸酯的史无前例的有机催化对映选择性级联迈克尔/半缩酮化/复古-羟醛反应。使用结合了（1 R，2 R）-1,2-二苯乙烷-1,2-二胺的双官能方胺催化剂，该反应可提供75-99％的收率和80-98％ee的产物。该过程为手性α-酮酯，3-芳基脯氨酸衍生物的前体，δ-氨基α-酮酸或环状α-酮内酰胺的合成提供了对映选择性的途径。
• Synthesis and Analgesic Activity of Etyl 4-[(4-Aryl-2-hydroxy-4-oxobut-2-enoyl)amino]benzoates
  作者：V. L. Gein、A. V. Romanova、O. V. Bobrovskaya、O. V. Nazarets、R. R. Makhmudov、Е. V. Gradova

  DOI：10.1134/s1070363222110056

  日期：2022.11

  4-aminobenzoic acid ethyl ester (benzocaine, anesthesin) in glacial acetic acid in the presence of anhydrous sodium acetate gave rise to ethyl (Z)-4-(4-aryl-2-hydroxy-4-oxobut-2-enamido)benzoates. Analgesic activity of the synthesized compounds was studied.

  摘要 4-芳基-2-羟基-4-氧代丁-2-烯酸甲酯（芳酰基丙酮酸）与 4-氨基苯甲酸乙酯（苯佐卡因，麻醉剂）在无水乙酸钠存在下在冰醋酸中反应得到上升为 ( Z )-4-(4-aryl-2-hydroxy-4-oxobut-2-enamido) 苯甲酸乙酯。研究了合成化合物的镇痛活性。
• Enantioselective [3 + 3] Annulation–Deoxalation Strategy for Rapid Access to δ-Oxoesters via N-Heterocyclic Carbene Catalysis
  作者：Izabela Barańska、Liliana Dobrzańska、Zbigniew Rafiński

  DOI：10.1021/acs.orglett.3c04397

  日期：2024.2.16

  unprecedented stereoselective synthetic approach to δ-oxoesters derivatives from readily available starting materials has been developed. This method, catalyzed by N-heterocyclic carbene, involves an annulation–deoxalation reaction of alkynyl aldehydes with 2,4-diketoesters and proceeds via the chiral α,β-unsaturated acylazolium intermediates. The annulation includes the in situ formation of dihydropyranones

  开发了一种新的、前所未有的立体选择性合成方法，从容易获得的起始材料中合成 δ-氧代酯衍生物。该方法由 N-杂环卡宾催化，涉及炔醛与 2,4-二酮酯的环化-脱草反应，并通过手性 α,β-不饱和酰唑鎓中间体进行。成环包括原位形成二氢吡喃酮，二氢吡喃酮在路易斯酸活化下进行开环甲醇分解，然后进行脱草作用，以中等至良好的收率得到手性 1,5-酮酯。