(E)-N,N-dimethyl-5-[2-(methylsulfonyl)vinyl]-1,4-di-p-tolyl-1H-pyrazole-3-carboxamide | 1414846-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-N,N-dimethyl-5-[2-(methylsulfonyl)vinyl]-1,4-di-p-tolyl-1H-pyrazole-3-carboxamide
• 英文别名: N,N-dimethyl-1,4-bis(4-methylphenyl)-5-[(E)-2-methylsulfonylethenyl]pyrazole-3-carboxamide
• CAS: 1414846-49-3
• 化学式: C₂₃H₂₅N₃O₃S
• 分子量: 423.536
• InChiKey: LMKYQECDHMDYGU-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1E,3Z)-1-methyl-4-(4-methylsulfanyl-2-nitrobuta-1,3-dien-1-yl)benzene 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (E)-N,N-dimethyl-5-[2-(methylsulfonyl)vinyl]-1,4-di-p-tolyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Highly-substituted pyrazoles and pyridazines by MIRC reactions of hydrazone anions and nitrobutadienic fragments

  摘要：

  In prosecution of the synthetic exploitation of nitrobutadienes deriving from the initial ring-opening of nitrothiophenes, their multifaceted behavior finds a further clear-cut example in their Michael-type acceptor reactivity toward the anions of alpha-oxohydrazones. Thus, depending on the starting diene, new poly-functionalized pyrazoles are obtained. Furthermore, most interestingly, in one occasion a dichotomy has been observed, depending on the nature of the Michael-type donor, leading with complete selectivity to either 5-member or 6-member N-heterocycles. The outcome encompasses motifs for both mechanistic and synthetic interest, for example, in the field of heterocycles endowed with possible pharmacological/biological activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.040

文献信息

• Synthesis of poly-functionalized pyrazoles and pyridazines from nitrobutadienes: an interesting dichotomy of practical relevance
  作者：Lara Bianchi、Alessandro Carloni-Garaventa、Massimo Maccagno、Marcella Pani、Giovanni Petrillo、Carlo Scapolla、Cinzia Tavani

  DOI：10.1016/j.tet.2015.08.014

  日期：2015.10

  The initial ring-opening of 3-nitrothiophene and further structural modifications lead to nitrobutadienic building-blocks whose synthetic usefulness in the field of heterocycles has been widely demonstrated. As a further example, the Michael addition of a hydrazone anion to the nitrovinyl moiety of nitrobutadienes generates 1,2-diazaheterocycles as the final result of an overall MIRC process. Depending on the nature of the substituents on the Michael-type acceptor and on the hydrazono nucleophile, an interesting dichotomy is observed that leads to either five-member or six-member N-heterocycles with complete selectivity. The results obtained appear to be both of mechanistic and synthetic interest e.g., in the field of heterocycles endowed with potential pharmacological/biological activity. (C) 2015 Elsevier Ltd. All rights reserved.