2-苄基-4-甲基-1H-吡唑-5-酮 | 53409-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-苄基-4-甲基-1H-吡唑-5-酮
• 英文名称: 1-benzyl-4-methyl-1,2-dihydro-pyrazol-3-one
• 英文别名: 1-benzyl-4-methyl-1H-pyrazol-3-ol；2-benzyl-4-methyl-1H-pyrazol-5-one
• CAS: 53409-18-0
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: FLTDBSDFIDXAFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-4-甲基-1H-吡唑-5-酮 在 sodium hydroxide 、 溴 、 碳酸氢钠 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 31.0h， 生成 2-(1-benzyl-4-bromo-4-methyl-5-oxopyrazol-3-yl)oxyacetic acid
  参考文献：
  名称：

  LINK Synthesis with 3-Hydroxy-1H-pyrazoles: 3-Carboxyisoalkyloxy-1H-pyrazoles - bicyclic acylpyrazolium salts and ?-Lactams - 3-Carboxyisoalkyloxy-4,5-dihydro-1H-pyrazol-5-ones

  摘要：

  1-Substituted 3-hydroxy-1H-pyrazoles 1 react with chloroform, NaOH, and aceton rasp. butan-2-one O-regio-specifically to yield 2-methyl-2-[(1H-pyrazol-3-yl)oxy]-propanoic resp. -butanoic acids 14 via a dichlorocarbene (12)-dichlorooxirane (9) pathway. Chlorides 17 of 14 easily cyclize to N-acylpyrazolium salts 18/19, which quantitatively afford esters 22-26 and amides 27-29 of 14. Enantiomers of the butanoic acid 14h, obtained via their diastereomeric cholesterol esters, differ in their stimulus to peroxisome proliferation. At 140 degrees C pyrazolium salts 18 undergo thermolysis to bicyclic beta-oxa-gamma-lactams 30-32. 3-Carboxyisoalkylamino-pyrazoles similarly give 1H-beta-aza-gamma-lactams 34. Reactions of 14 with surplus SOCl2 result in 6-chloro- 37 resp. 7-chloro-beta-oxa-gamma-lactams 38 via chlorosulfinylation and extrusion of SO, and in 4,4-bispyrazolyl-sulfoxide 39. A mild introduction of additional O-functions into pyrazoles affording 4,5-dihydro-3-hydroxy-5-oxo-1H-pyrazoles 52-57 is presented. Biological effects of the new pyrazoles are protection against shock and ADP-induced thromboembolism, reduction of serum lipids and improvement of blood flow.

  DOI：

  10.1002/prac.19983400506
• 作为产物：
  描述：

  以 丙酮 为溶剂， 反应 10.0h， 生成 2-苄基-4-甲基-1H-吡唑-5-酮
  参考文献：
  名称：

  LINK Synthesis with 3-Hydroxy-1H-pyrazoles: 3-Carboxyisoalkyloxy-1H-pyrazoles - bicyclic acylpyrazolium salts and ?-Lactams - 3-Carboxyisoalkyloxy-4,5-dihydro-1H-pyrazol-5-ones

  摘要：

  1-Substituted 3-hydroxy-1H-pyrazoles 1 react with chloroform, NaOH, and aceton rasp. butan-2-one O-regio-specifically to yield 2-methyl-2-[(1H-pyrazol-3-yl)oxy]-propanoic resp. -butanoic acids 14 via a dichlorocarbene (12)-dichlorooxirane (9) pathway. Chlorides 17 of 14 easily cyclize to N-acylpyrazolium salts 18/19, which quantitatively afford esters 22-26 and amides 27-29 of 14. Enantiomers of the butanoic acid 14h, obtained via their diastereomeric cholesterol esters, differ in their stimulus to peroxisome proliferation. At 140 degrees C pyrazolium salts 18 undergo thermolysis to bicyclic beta-oxa-gamma-lactams 30-32. 3-Carboxyisoalkylamino-pyrazoles similarly give 1H-beta-aza-gamma-lactams 34. Reactions of 14 with surplus SOCl2 result in 6-chloro- 37 resp. 7-chloro-beta-oxa-gamma-lactams 38 via chlorosulfinylation and extrusion of SO, and in 4,4-bispyrazolyl-sulfoxide 39. A mild introduction of additional O-functions into pyrazoles affording 4,5-dihydro-3-hydroxy-5-oxo-1H-pyrazoles 52-57 is presented. Biological effects of the new pyrazoles are protection against shock and ADP-induced thromboembolism, reduction of serum lipids and improvement of blood flow.

  DOI：

  10.1002/prac.19983400506

文献信息

• Begtrup, Mikael; Vedso, Per, Journal of the Chemical Society. Perkin transactions I, 1992, # 19, p. 2555 - 2564
  作者：Begtrup, Mikael、Vedso, Per

  DOI：——

  日期：——
• Begtrup Mikael, Vedso Per, J. Chem. Soc. Perkin Trans. 1, (1992) N 19, S 2555-2563
  作者：Begtrup Mikael, Vedso Per

  DOI：——

  日期：——
• ——
  作者：DORN H.、 OZEGOWSKI R.

  DOI：——

  日期：——