(E)-3-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5-dimethyl-1H-pyrazole | 1018767-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5-dimethyl-1H-pyrazole
• 英文别名: 3-(3-methoxy-4-hydroxy-styryl)-4,5-dimethyl-1H-pyrazole；4-[(E)-2-(4,5-dimethyl-1H-pyrazol-3-yl)ethenyl]-2-methoxyphenol
• CAS: 1018767-20-8
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: VWIIDPQXPFILEL-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-6-(4-hydroxy-3-methoxyphenyl)-3-methylhex-5-ene-2,4-dione 在 肼 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以61%的产率得到(E)-3-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  The annular tautomerism of the curcuminoid NH-pyrazoles

  摘要：

  四种 NH 吡唑的结构：(E)-3,5-双[β-(4-羟基-3-甲氧基苯基)-乙烯基]-1H-吡唑 (3)、(E)-3(5)-[β-(4-羟基-3-甲氧基苯基)-乙烯基]-5(3)-甲基-1H-吡唑 (4)、(E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) 和 (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8) 已通过 X 射线晶体学测定。含有苯酚残基的化合物在结晶时会形成薄片，这些薄片通过独特的同分异构体（4）或两种同分异构体（5）的 2:1 混合物（3 的同分异构体完全相同）之间复杂的氢键模式来稳定。缺乏羟基的吡唑 8 结晶为环状二聚体，通过 N-H⋯N 氢键稳定。13C 和 15N CPMAS NMR 光谱测定了溶液和固态中的同分异构现象。对于化合物 4、5 和 8，固态结果与晶体学观察到的结果一致；溶液中含量最高的同分异构体与固态中的同分异构体（4 和 8）或晶体中含量最高的同分异构体（5）一致。

  DOI：

  10.1039/b812018h

文献信息

• Synthesis and biological evaluation of curcuminoid pyrazoles as new therapeutic agents in inflammatory bowel disease: Effect on matrix metalloproteinases
  作者：R.M. Claramunt、L. Bouissane、M.P. Cabildo、M.P. Cornago、J. Elguero、A. Radziwon、C. Medina

  DOI：10.1016/j.bmc.2008.12.029

  日期：2009.2

  Seven N-unsubstituted curcuminoid pyrazoles have been synthesized from the corresponding beta-diketones ( including curcumin). We evaluated the possibility of curcuminoid pyrazoles regulating the activity of matrix metalloproteinases ( MMPs) by human intestinal epithelial cells in vitro. Zymographic analysis revealed that three compounds significantly down-regulated MMP-9 activity on inflammation-induced intestinal epithelial cells, making them original candidates for the treatment of inflammatory bowel disease (IBD). (c) 2008 Elsevier Ltd. All rights reserved.
• The annular tautomerism of the curcuminoid NH-pyrazoles
  作者：Pilar Cornago、Pilar Cabildo、Rosa M. Claramunt、Latifa Bouissane、Elena Pinilla、M. Rosario Torres、José Elguero

  DOI：10.1039/b812018h

  日期：——

  The structures of four NH-pyrazoles, (E)-3,5-bis[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-1H-pyrazole (3), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-5(3)-methyl-1H-pyrazole (4), (E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) and (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8), have been determined by X-ray crystallography. Compounds that have a phenol residue crystallize forming sheets that are stabilized by a complex pattern of hydrogen bonds between a unique tautomer (4), or by a 2 : 1 mixture of both tautomers (5) (these tautomers being identical in the case of 3). Pyrazole 8, which lacks OH groups, crystallizes in cyclic dimers that are stabilized by N–H⋯N hydrogen bonds. The tautomerism in solution and in the solid state was determined by 13C and 15N CPMAS NMR spectroscopy. For compounds 4, 5 and 8, the solid state results agree with those observed by crystallography; the most abundant tautomer in solution coincides with the tautomer present in the solid state (4 and 8) or with the most abundant tautomer in the crystal (5).

  四种 NH 吡唑的结构：(E)-3,5-双[β-(4-羟基-3-甲氧基苯基)-乙烯基]-1H-吡唑 (3)、(E)-3(5)-[β-(4-羟基-3-甲氧基苯基)-乙烯基]-5(3)-甲基-1H-吡唑 (4)、(E)-3(5)-[β-(4-hydroxy-3-methoxyphenyl)-ethenyl]-4,5(3)-dimethyl-1H-pyrazole (5) 和 (E)-3(5)-[β-(3,4-dimethoxyphenyl)-ethenyl]-4-methyl-5(3)-phenyl-1H-pyrazole (8) 已通过 X 射线晶体学测定。含有苯酚残基的化合物在结晶时会形成薄片，这些薄片通过独特的同分异构体（4）或两种同分异构体（5）的 2:1 混合物（3 的同分异构体完全相同）之间复杂的氢键模式来稳定。缺乏羟基的吡唑 8 结晶为环状二聚体，通过 N-H⋯N 氢键稳定。13C 和 15N CPMAS NMR 光谱测定了溶液和固态中的同分异构现象。对于化合物 4、5 和 8，固态结果与晶体学观察到的结果一致；溶液中含量最高的同分异构体与固态中的同分异构体（4 和 8）或晶体中含量最高的同分异构体（5）一致。