(4S,5R)-1-(4-bromophenyl)-4,5-dihydro-4-methyl-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole

• 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-4-methyl-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole
• 英文别名: 3-[(3R,4S)-2-(4-bromophenyl)-4-methyl-5-phenyl-3,4-dihydropyrazole-3-carbonyl]-1,3-oxazolidin-2-one
• 化学式: C₂₀H₁₈BrN₃O₃
• 分子量: 428.285
• InChiKey: AKYHORDDIWTBFF-FZKQIMNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-4-methyl-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以64 mg的产率得到(4S,5R)-1-(4-bromophenyl)-4,5-dihydro-5-hydroxymethyl-4-methyl-3-phenyl-1H-pyrazole
  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：

  N-(4-bromo-phenyl)-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 在 N,N-二异丙基乙胺 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 4 A molecular sieve 、 magnesium triflimide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (4S,5R)-1-(4-bromophenyl)-4,5-dihydro-4-methyl-5-(oxazolidin-2-one-3-carbonyl)-3-phenyl-1H-pyrazole
  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.