1-(2,4-dinitrophenyl)-5-<(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl>-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: 1-(2,4-dinitrophenyl)-5-<(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl>-1H-pyrazole
• 英文别名: 1-(2,4-dinitrophenyl)-5-[2-(2,2,6-trimethyl-2-cyclohexen-1-yl)ethenyl]-1H-pyrazole；1-(2,4-dinitrophenyl)-5-[2-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl]-1H-pyrazole；1-(2,4-dinitrophenyl)-5-[(E)-2-(2,6,6-trimethylcyclohex-2-en-1-yl)vinyl]pyrazole；1-(2,4-dinitrophenyl)-5-[(E)-2-(2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl]pyrazole
• 化学式: C₂₀H₂₂N₄O₄
• 分子量: 382.419
• InChiKey: RZORGLQDNCEVHJ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二硝基苯肼 、 3-dimethylamino-5-(2,2,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal 在 硫酸 作用下， 以 乙醇 为溶剂， 以81%的产率得到1-(2,4-dinitrophenyl)-5-<(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenyl>-1H-pyrazole
  参考文献：
  名称：

  类视黄醇的新杂环衍生物的合成

  摘要：

  α-和β-紫罗兰酮1和2与二烷基甲酰胺/氯氧化磷的反应提供烯胺6和7以及预期的氯衍生物4和5。的反应图6a与肼，羟胺和胍配吡唑，异恶唑，嘧啶8-10示出这些烯胺酮如在合成类视黄醇的合成中的关键中间体的潜力。

  DOI：

  10.1002/jhet.5570350626

文献信息

• Synthesis of new heterocyclic derivatives of retinoids
  作者：Enzo Sottofattori、Maria Anzaldi、Alessandro Balbi

  DOI：10.1002/jhet.5570350626

  日期：1998.11

  Reaction of α- and β-ionones 1 and 2 with dialkylformamide/phosphorus oxychloride affords enamines 6 and 7 along with the expected chloro derivatives 4 and 5. Reaction of 6a with hydrazines, hydroxylamine and guanidine furnished pyrazoles, isoxazole, pyrimidine 8–10 showing the potential of these enaminones as key intermediates in the synthesis of synthetic retinoids.

  α-和β-紫罗兰酮1和2与二烷基甲酰胺/氯氧化磷的反应提供烯胺6和7以及预期的氯衍生物4和5。的反应图6a与肼，羟胺和胍配吡唑，异恶唑，嘧啶8-10示出这些烯胺酮如在合成类视黄醇的合成中的关键中间体的潜力。
• Synthesis and antimicrobial activity of heterocyclic ionone-like derivatives
  作者：M Anzaldi

  DOI：10.1016/s0223-5234(99)00209-3

  日期：1999.10

  A number of heterocyclic ionone-like derivatives 5 were prepared with appropriate bifunctional reagents by one-pot cyclisation of 3-dimethylamino-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal 3a, which was, in turn, obtained from alpha-ionone with N,N-dimethylformamide/phosphorus oxychloride. All compounds 5 possess remarkable activity against the selected Gram-positive, Gramnegative bacterial strains and against Candida albicans. Derivatives 5a2 and 5a6, acting at a high level especially against both Propionibacterium acnes and Staphylococcus aureus, could play a potential role in the treatment of acne and related skin disorders. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Synthesis and biological evaluation of novel heterocyclic ionone-like derivatives as anti-inflammatory agents
  作者：Alessandro Balbi、Maria Anzaldi、Mauro Mazzei、Mariangela Miele、Maria Bertolotto、Luciano Ottonello、Franco Dallegri

  DOI：10.1016/j.bmc.2006.04.007

  日期：2006.8

  Five- and six-membered heterocyclic ionone-like derivatives 4-6 have been synthesised in one step and with good yield from the key intermediate 3a and appropriate bifunctional reagents. Four were active as inhibitors of the respiratory burst of human neutrophils without affecting cell viability. The two most active compounds (5a,d) tested in neutrophil migration assays, were also found to be potent inhibitors of neutrophil chemotactic responsiveness. These two molecules could be considered as lead compounds of new drugs which can be an effective tool to treat psoriasis and related neutrophilic dermatoses. (c) 2006 Elsevier Ltd. All rights reserved.