4-(2-hydroxy-4-methoxyphenyl)-4-oxobutanoic acid | 14617-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-hydroxy-4-methoxyphenyl)-4-oxobutanoic acid
• 英文别名: 2'-hydroxy-4'-methoxy-3-benzoyl-propionic acid；4-(2-hydroxy-4-methoxy-phenyl)-4-oxo-butyric acid；4-(2-Hydroxy-4-methoxy-phenyl)-4-oxo-buttersaeure；β-(2-Oxy-4-methoxy-benzoyl)-propionsaeure；4-(2-Hydroxy-4-methoxy-phenyl)-4-oxo-propionsaeure；4-(2'-Hydroxy-4'-methoxyphenyl)-4-oxobutansaeure
• CAS: 14617-02-8
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: MMMHZBODZRNHIN-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C(Solv: water (7732-18-5))
• 沸点：
  465.8±35.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-4-methoxyphenyl)-4-oxobutanoic acid 生成 4-(2-hydroxy-4-methoxy-phenyl)-4-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  Dalal; Nargund, Journal of the Indian Chemical Society, 1937, vol. 14, p. 406,409

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯二酚 在 乙醚 、 zinc(II) chloride 作用下， 生成 4-(2-hydroxy-4-methoxyphenyl)-4-oxobutanoic acid
  参考文献：
  名称：

  Dalal; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1938, vol. 7/3, p. 189

  摘要：

  DOI：

文献信息

• Die Reduktion von β-Benzoyl-propionsäuren aus der Reihe des Resorcins
  作者：F. Zymalkowski、J. Gelberg

  DOI：10.1002/ardp.19662990614

  日期：——

  mit NaBH4 bis zur Stufe der Hydroxysaure reduzieren. Die Ursachen werden diskutiert. Die elektrolytische Reduktion von Succinoylphenolen an einer Bleikathode liefert neben γ-Aryl-γ-hydroxybuttersauren deren pinacolartige Dimerisate, die durch Protonenkatalyse lactonisiert werden. 4-Methoxyphenyl-butyrolacton kann mit BBr3 entmethyliert werden. Die Reaktion last sich nicht auf 4-Methoxy-2-hydroxyphenyl-butyrolacton

  与其两种半醚和许多其他琥珀酰苯酚相比，2,4-二羟基-苯甲酰丙酸（琥珀酰间苯二酚）不能通过催化或用 NaBH4 还原到羟基酸的水平。原因进行了讨论。铅阴极上琥珀酰苯酚的电解还原不仅产生 γ-芳基-γ-羟基丁酸，而且产生它们的频哪醇样二聚体，它们通过质子催化内酯化。4-甲氧基苯基丁内酯可以用 BBr3 去甲基化。该反应不适用于 4-甲氧基-2-羟基苯基-丁内酯。
• 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。
• Acetaldehyde stimulation of the growth of Saccharomyces cerevisiae in the presence of inhibitors found inlignocellulose-to-ethanol fermentations
  作者：A R Barber、H Hansson、N B Pamment

  DOI：10.1038/sj.jim.7000031

  日期：2000.8.1

  The addition of small quantities of acetaldehyde to fermentations containing inhibitory concentrations of furfural, acetate and other compounds typically present in lignocellulosic hydrolyzates significantly reduced the lag phase of yeast growth and stimulated ethanol production. Similar effects were observed when acetaldehyde (0.06 g l−1) was added to fermentations of a birch wood hydrolyzate produced by steam/acid pretreatment. Acetaldehyde addition appears to have potential as a low-cost alternative (or adjunct) to current procedures for medium detoxification in lignocellulose-to-ethanol fermentations, particularly those in which high inhibitor concentrations are generated through recycling of the culture broth. Journal of Industrial Microbiology & Biotechnology (2000) 25, 104–108.

  在含有抑制浓度的糠醛、乙酸盐和木质纤维素水解物中通常存在的其他化合物的发酵中加入少量乙醛，可显著减少酵母生长的滞后期，并促进乙醇的产生。在通过蒸汽/酸预处理生产的桦木水解物的发酵过程中加入乙醛（0.06 克/升），也能观察到类似的效果。在木质纤维素制乙醇发酵过程中，特别是在通过循环培养液产生高浓度抑制剂的发酵过程中，添加乙醛似乎有可能成为当前培养基解毒程序的低成本替代品（或辅助品）。工业微生物学与生物技术杂志》（2000 年）25 期，104-108 页。
• Synthesis and pharmacological evaluation of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3(2H)-ones bioisosters of antihypertensive and antithrombotic benzo[h]cinnolinones
  作者：G Cignarella、D Barlocco、MM Curzu、GA Pinna、P Cazzulani、M Cassin、B Lumachi

  DOI：10.1016/0223-5234(90)90194-8

  日期：1990.11

  A series of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3-(2H)-ones (2a-h), have been prepared and evaluated for their pharmacological profile as antihypertensive and antithrombotic agents. Compounds 2 were ineffective in lowering the blood pressure of spontaneously hypertensive rats (SHR), only 2c (R1 = NHCOCH3) showing a short lasting action (< 2 h). Compounds 2c and 2b (R1 = NH2) were found to be very active as antithrombotic agents in mice, being more potent than acetylsalicylic acid (ASA) taken as reference drug. Moreover, many derivatives of this class protected rats from formation of ASA or phenylbutazone (PBZ) induced ulcers, the most active being 2f (R2 = OCH3) (ED50 = 12.2 mg/kg and 25.4 mg/kg po in ASA and PBZ models, respectively).
• Perkin; Robinson, Journal of the Chemical Society, 1908, vol. 93, p. 513
  作者：Perkin、Robinson

  DOI：——

  日期：——