5-Amino-1-[2-(4-methylphenyl)-2-oxoethyl]-3-phenylpyrazole-4-carbonitrile | 851707-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Amino-1-[2-(4-methylphenyl)-2-oxoethyl]-3-phenylpyrazole-4-carbonitrile
• CAS: 851707-85-2
• 化学式: C₁₉H₁₆N₄O
• 分子量: 316.362
• InChiKey: MZZHHFNCSSBDKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Amino-1-[2-(4-methylphenyl)-2-oxoethyl]-3-phenylpyrazole-4-carbonitrile 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1H‐Imidazo[1,2‐b]‐pyrazole by the Cyclocondensation Between 5‐Amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole and α‐Tosyloxyacetophenones or α‐Haloacetophenones

  摘要：

  A series of new 7-cyano-6-phenyl-2-aryl-IH-imidazo[1,2-b]pyrazoles (5) by the cyclocondensation reactions between 5-amino-4-cyano-3-phenyl-1H-pyrazole (1) and alpha-bromoacetophenones (3) or alpha-tosyloxyacetophenones (2) obtained by the reactions of acetophenones with [hydroxy(tosyloxy)iodo]benzene (HTIB) have been synthesized in good yields, and the intermediates 5-amino-4-cyano-6-phenyl-1-(aroylmethyi)pyrazoles (4) were isolated as a potent evidence for the regioselectivity. The syntheses of 4 and 5 have been achieved successfully through the procedure involving alpha-tosyloxyacetophenones and some through the procedure involving alpha-bromoacetophenones. When utilizing a-tosyloxyacetophenones, the reactions were more eco-friendly, the reaction time was significantly reduced, and the synthetic procedure was more convenient and easier to manipulate.

  DOI：

  10.1081/scc-200049761
• 作为产物：
  描述：

  对甲基苯乙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.75h， 生成 5-Amino-1-[2-(4-methylphenyl)-2-oxoethyl]-3-phenylpyrazole-4-carbonitrile
  参考文献：
  名称：

  Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1H‐Imidazo[1,2‐b]‐pyrazole by the Cyclocondensation Between 5‐Amino‐4‐cyano‐3‐phenyl‐1H‐pyrazole and α‐Tosyloxyacetophenones or α‐Haloacetophenones

  摘要：

  A series of new 7-cyano-6-phenyl-2-aryl-IH-imidazo[1,2-b]pyrazoles (5) by the cyclocondensation reactions between 5-amino-4-cyano-3-phenyl-1H-pyrazole (1) and alpha-bromoacetophenones (3) or alpha-tosyloxyacetophenones (2) obtained by the reactions of acetophenones with [hydroxy(tosyloxy)iodo]benzene (HTIB) have been synthesized in good yields, and the intermediates 5-amino-4-cyano-6-phenyl-1-(aroylmethyi)pyrazoles (4) were isolated as a potent evidence for the regioselectivity. The syntheses of 4 and 5 have been achieved successfully through the procedure involving alpha-tosyloxyacetophenones and some through the procedure involving alpha-bromoacetophenones. When utilizing a-tosyloxyacetophenones, the reactions were more eco-friendly, the reaction time was significantly reduced, and the synthetic procedure was more convenient and easier to manipulate.

  DOI：

  10.1081/scc-200049761

文献信息

• Hypervalent Iodine in Synthesis: A Novel Two‐Step Procedure for the Synthesis of New Derivatives of 1<i>H</i>‐Imidazo[1,2‐b]‐pyrazole by the Cyclocondensation Between 5‐Amino‐4‐cyano‐3‐phenyl‐1<i>H</i>‐pyrazole and α‐Tosyloxyacetophenones or α‐Haloacetophenones
  作者：Li Ming、Zhao Guilong、Wen Lirong、Yang Huazheng

  DOI：10.1081/scc-200049761

  日期：2005.3

  A series of new 7-cyano-6-phenyl-2-aryl-IH-imidazo[1,2-b]pyrazoles (5) by the cyclocondensation reactions between 5-amino-4-cyano-3-phenyl-1H-pyrazole (1) and alpha-bromoacetophenones (3) or alpha-tosyloxyacetophenones (2) obtained by the reactions of acetophenones with [hydroxy(tosyloxy)iodo]benzene (HTIB) have been synthesized in good yields, and the intermediates 5-amino-4-cyano-6-phenyl-1-(aroylmethyi)pyrazoles (4) were isolated as a potent evidence for the regioselectivity. The syntheses of 4 and 5 have been achieved successfully through the procedure involving alpha-tosyloxyacetophenones and some through the procedure involving alpha-bromoacetophenones. When utilizing a-tosyloxyacetophenones, the reactions were more eco-friendly, the reaction time was significantly reduced, and the synthetic procedure was more convenient and easier to manipulate.