5-(N-Acetylamino)-1-ethyl-3-methylpyrazole | 260442-60-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(N-Acetylamino)-1-ethyl-3-methylpyrazole
• 英文别名: N-(2-ethyl-5-methylpyrazol-3-yl)acetamide
• CAS: 260442-60-2
• 化学式: C₈H₁₃N₃O
• 分子量: 167.211
• InChiKey: LHWAZWZJZIOBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(N-Acetylamino)-1-ethyl-3-methylpyrazole 在 硫酸 、 碘 、 碘酸 作用下， 以 水 、 溶剂黄146 、 苯 为溶剂， 反应 2.0h， 以6.34 g的产率得到5-(N-Acetylamino)-1-ethyl-4-iodo-3-methylpyrazole
  参考文献：
  名称：

  Synthesis of vicinal aminoiodo- and (acetylamino)iodo-l-alkylpyrazoles

  摘要：

  3- and 5-(Acetylamino)-4-iodo-1-alkylpyrazoles were obtained by successive acylation and iodination from 3- and 5-amino-1-alkylpyrazoles without isolating intermediate (acetylamino)pyrazoles. 3- and 5-Iodo- and 3,5-diiodo-4-amino-1-methylpyrazoles were synthesized from appropriate iodonitropyrazoles by reduction with SnCl2 in HCl.

  DOI：

  10.1007/bf01431121
• 作为产物：
  描述：

  5-(N-Acetylamino)-1-ethyl-4-iodo-3-methylpyrazole 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 、 4-乙炔基苯甲醚 作用下， 反应 5.0h， 以86%的产率得到5-(N-Acetylamino)-1-ethyl-3-methylpyrazole
  参考文献：
  名称：

  Peculiarities of copper(I)- and palladium-catalyzed cross-coupling of terminal alkynes with vicinal amino- and (N-acetylamino)-iodopyrazoles. Synthesis of alkynylaminopyrazoles

  摘要：

  通过使用Pd(PPh3)2Cl2和CuI作为催化剂在Et3N中，或与铜炔化物的组合，合成了一系列邻位氨基和（N-乙酰氨基）烷基吡唑。这种铜炔化物与这些氨基和（N-乙酰氨基）碘吡唑的斯蒂芬斯-卡斯特罗反应被确立为制备（N-乙酰氨基）炔基吡唑的常用方法。使用Pd/Cu催化的碘吡唑（索诺加希拉反应）与具有电子供给取代基的烷-1-炔的交叉耦合不适合合成炔基吡唑：3-和5-碘吡唑不反应，但在4-碘衍生物的情况下，只有还原去碘反应发生，同时伴随烷-1-炔组分的同偶联反应。

  DOI：

  10.1039/a903754c

文献信息

• Peculiarities of copper(I)- and palladium-catalyzed cross-coupling of terminal alkynes with vicinal amino- and (N-acetylamino)-iodopyrazoles. Synthesis of alkynylaminopyrazoles
  作者：Eugene V. Tretyakov、David W. Knight、Sergei F. Vasilevsky

  DOI：10.1039/a903754c

  日期：——

  A number of vicinal amino- and (N-acetylamino)-alkylpyrazoles have been synthesized by cross-coupling reactions of iodopyrazoles with alk-1-ynes using a combination of Pd(PPh3)2Cl2 and CuI as catalyst in Et3N or with copper acetylides. The latter Stephens–Castro reaction of copper acetylides with these amino- and (N-acetylamino)-iodopyrazoles was established as a common method for the preparation of (N-acetylamino)alkynylpyrazoles. The Pd/Cu-catalyzed cross-coupling of iodopyrazoles (Sonogashira reaction) with alk-1-ynes bearing electron-releasing substituents was unsuitable for the synthesis of alkynylpyrazoles: 3- and 5-iodopyrazoles were unreactive but, in the case of 4-iodo derivatives, reductive deiodination, accompanied by homocoupling of the alk-1-yne component, was the only reaction.

  通过使用Pd(PPh3)2Cl2和CuI作为催化剂在Et3N中，或与铜炔化物的组合，合成了一系列邻位氨基和（N-乙酰氨基）烷基吡唑。这种铜炔化物与这些氨基和（N-乙酰氨基）碘吡唑的斯蒂芬斯-卡斯特罗反应被确立为制备（N-乙酰氨基）炔基吡唑的常用方法。使用Pd/Cu催化的碘吡唑（索诺加希拉反应）与具有电子供给取代基的烷-1-炔的交叉耦合不适合合成炔基吡唑：3-和5-碘吡唑不反应，但在4-碘衍生物的情况下，只有还原去碘反应发生，同时伴随烷-1-炔组分的同偶联反应。
• Synthesis of vicinal aminoiodo- and (acetylamino)iodo-l-alkylpyrazoles
  作者：E. V. Tret'yakov、S. F. Vasitevsky

  DOI：10.1007/bf01431121

  日期：1996.11

  3- and 5-(Acetylamino)-4-iodo-1-alkylpyrazoles were obtained by successive acylation and iodination from 3- and 5-amino-1-alkylpyrazoles without isolating intermediate (acetylamino)pyrazoles. 3- and 5-Iodo- and 3,5-diiodo-4-amino-1-methylpyrazoles were synthesized from appropriate iodonitropyrazoles by reduction with SnCl2 in HCl.