(4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester | 858342-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3R,4S)-2-(4-bromophenyl)-3-(2-oxo-1,3-oxazolidine-3-carbonyl)-5-phenyl-3,4-dihydropyrazole-4-carboxylate
• CAS: 858342-84-4
• 化学式: C₂₄H₂₄BrN₃O₅
• 分子量: 514.376
• InChiKey: RREWXYFQIKFEEY-UYAOXDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-hydroxymethyl-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An Entry to a Chiral Dihydropyrazole Scaffold:  Enantioselective [3 + 2] Cycloaddition of Nitrile Imines

  摘要：

  We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared.

  DOI：

  10.1021/ja051650b
• 作为产物：
  描述：

  富马酸叔-丁酯 在 N,N-二异丙基乙胺 草酰氯 、 4 A molecular sieve 、 sodium hydride 、 N,N-二甲基甲酰胺 、 magnesium triflimide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.92h， 生成 (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An Entry to a Chiral Dihydropyrazole Scaffold:  Enantioselective [3 + 2] Cycloaddition of Nitrile Imines

  摘要：

  We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared.

  DOI：

  10.1021/ja051650b

文献信息

• An Entry to a Chiral Dihydropyrazole Scaffold:  Enantioselective [3 + 2] Cycloaddition of Nitrile Imines
  作者：Mukund P. Sibi、Levi M. Stanley、Craig P. Jasperse

  DOI：10.1021/ja051650b

  日期：2005.6.1

  We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared.