2-(1-Benzyl-4-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yloxy)-2-methyl-propionic acid | 212191-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(1-Benzyl-4-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yloxy)-2-methyl-propionic acid
• 英文别名: 2-[(1-benzyl-4-methyl-5-oxo-4H-pyrazol-3-yl)oxy]-2-methylpropanoic acid
• CAS: 212191-01-0
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: JTNDPXDOOVPWNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-Benzyl-4-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yloxy)-2-methyl-propionic acid 在 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 生成 2-[(4S,4'R)-1,1'-Dibenzyl-3'-(1-carboxy-1-methyl-ethoxy)-4,4'-dimethyl-5,5'-dioxo-4,5,4',5'-tetrahydro-1H,1'H-[4,4']bipyrazolyl-3-yloxy]-2-methyl-propionic acid 、 2-[(4S,4'S)-1,1'-Dibenzyl-3'-(1-carboxy-1-methyl-ethoxy)-4,4'-dimethyl-5,5'-dioxo-4,5,4',5'-tetrahydro-1H,1'H-[4,4']bipyrazolyl-3-yloxy]-2-methyl-propionic 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：

  2-甲基-2-[[4-甲基-1-苄基-1H-吡唑-3-基]氧基]丙酸 在 sodium hydroxide 、 溴 、 碳酸氢钠 、 三乙胺 、 维生素 C 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(1-Benzyl-4-methyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yloxy)-2-methyl-propionic 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

文献信息

• 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
  作者：Helmut Dorn、R�diger Ozegowski

  DOI：10.1002/prac.19983400506

  日期：——

  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.