4-(2-hydroxy-5-methylphenyl)-4-oxobutanoic acid | 103987-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-hydroxy-5-methylphenyl)-4-oxobutanoic acid
• 英文别名: 4-(2-hydroxy-5-methyl-phenyl)-4-oxo-butyric acid；4-(2-Hydroxy-5-methyl-phenyl)-4-oxo-buttersaeure；3-(5-methyl-2-hydroxybenzoyl)-propionic acid
• CAS: 103987-17-3
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: NUMGKJNSGGELIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-5-methylphenyl)-4-oxobutanoic acid 在 盐酸 、 amalgamated zinc 、 溶剂黄146 作用下， 生成 4-(2-methoxy-5-methyl-phenyl)-butyric acid
  参考文献：
  名称：

  Synthesis and Rearrangement of Cyclohexadienones

  摘要：

  DOI：

  10.1021/ja01157a129
• 作为产物：
  描述：

  Methyl 4-(2-Hydroxy-5-methylphenyl)-4-oxobutanoate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-(2-hydroxy-5-methylphenyl)-4-oxobutanoic acid
  参考文献：
  名称：

  Photochemische und Aluminiumchlorid-katalysierte Friessche Umlagerung von Bernsteins�uremonoarylestern. Synthese von 2(3H)-Furanonen

  摘要：

  DOI：

  10.1007/bf00811125

文献信息

• Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes
  作者：Rainer Mahrwald、Celin Richter、Nikolaus Ernsting

  DOI：10.1055/s-0035-1561370

  日期：——

  observed during a Friedel–Crafts acylation/demethylation cascade. In contrast to this cascade, oxygen-containing acylating reagents do not undergo the demethylation step. By the methodology elaborated here, an access is provided to important intermediates for the total synthesis of seminaphthorhodafluor (SNARF) dyes. High selectivity is observed during a Friedel–Crafts acylation/demethylation cascade

  摘要 在Friedel-Crafts酰化/去甲基化级联反应中观察到高选择性。与该级联反应相反，含氧的酰化剂不进行脱甲基步骤。通过此处阐述的方法，可以为重要的中间体提供全萘四氟（SNARF）染料的全合成。 在Friedel-Crafts酰化/去甲基化级联反应中观察到高选择性。与该级联反应相反，含氧的酰化剂不进行脱甲基步骤。通过此处阐述的方法，可以为重要的中间体提供全萘四氟（SNARF）染料的全合成。
• Pyridazinethiones
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04111936A1

  公开（公告）日：1978-09-05

  Substituted phenyl pyridazinethiones which are useful intermediates in the preparation of substituted phenylhydrazinopyridazines which have .beta.-adrenergic blocking and vasodilator activity.

  取代苯基吡啶硫酮是制备取代苯基肼吡啶类化合物的有用中间体，这些化合物具有β-肾上腺素能受体阻滞和血管扩张活性。
• The Fries Reaction
  作者：ABDEL FATTAH MAREY、FAWZY G. BADDAR、WILLIAM I. AWAD

  DOI：10.1038/1721186a0

  日期：1953.12

  effect of medium on the rearrangement of phenyl (I; R=H)- and p-cresyl(I ; R=CH3)-hydrogen succinate in presence of anhydrous aluminium chloride has been carried out. The reaction was accomplished under standardized conditions using a constant temperature (117°, boiling n-butyl alcohol bath) for 2½ hr., the same molecular proportion of the ester (0.033 mole), aluminium chloride (0.067 mole) and the solvent

  继续对 Fries 反应机理的研究 1，系统研究介质对苯基 (I; R=H)- 和对甲酚 (I; R=CH3)-琥珀酸氢盐重排的影响已进行无水氯化铝。该反应在标准条件下使用恒温（117°，沸腾的正丁醇浴）进行 2.5 小时，相同分子比例的酯（0.033 摩尔）、氯化铝（0.067 摩尔）和溶剂（0.462痣）。结果总结在表1中。
• Khan; Siddiqui, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 8, p. 614 - 619
  作者：Khan、Siddiqui

  DOI：——

  日期：——
• Synthesis, antiproliferative and anti-inflammatory activities of some novel 6-aryl-2-(p-(methanesulfonyl)phenyl)-4,5-dihydropyridazi-3(2H)-ones
  作者：Syed Ovais、Kalim Javed、Shafiya Yaseen、Rafia Bashir、Pooja Rathore、Raed Yaseen、Alhamzah D. Hameed、Mohammad Samim

  DOI：10.1016/j.ejmech.2013.06.050

  日期：2013.9

  Sixteen new 6-aryl-2-(p-(methanesulfonyl)phenyl)-4,5-dihydropyridazi-3(2H)-ones (2a-p) were synthesized and tested for in vitro anticancer and in vivo anti-inflammatory activities. Eleven (2b, 2d, 2e-j and 2m-p) of the obtained compounds were screened for their antiproliferative activity towards 60 human cancer cell lines by the National Cancer Institute (USA). Compound 2f showed remarkable activity with GI(50) less than 1 mu M on 36 human tumor cell lines and has been referred to Biological Evaluation Committee (NCI) for advance study. Compound 2g also displayed promising antiproliferative activity against 20 different cell lines with GI(50) less than 1 mu M. Compounds 2k and 2n were found to have a comparable anti-inflammatory activity to that of standard drug etoricoxib in carrageenan-induced rat hind paw edema model at 5 h. (C) 2013 Elsevier Masson SAS. All rights reserved.