1,4-dimethoxy-2-(3,5-dimethylpyrazol-1-yl)benzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dimethoxy-2-(3,5-dimethylpyrazol-1-yl)benzene
• 英文别名: 2-(3,5-dimethylpyrazol-1-yl)-1,4-dimethoxybenzene；1-(2,5-dimethoxyphenyl)-3,5-dimethyl-1H-pyrazole；1-(2,5-dimethoxyphenyl)-3,5-dimethyl-1H-pyrazol；1-(2,5-dimethoxyphenyl)-3,5-dimethylpyrazole
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: NPOZNJGLBIUCIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲基吡唑 、 对苯二甲醚 在 2,3,5-三甲基吡啶 作用下， 以 甲醇 为溶剂， 以57%的产率得到1,4-dimethoxy-2-(3,5-dimethylpyrazol-1-yl)benzene
  参考文献：
  名称：

  Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene

  摘要：

  在 MeOH 中，通过在铂电极上进行不分裂的安培静态电解，研究了 1,4 二甲基苯与偶氮唑（吡唑、三唑及其衍生物以及四唑）的反应。该过程以 1,1,4- 三甲氧基壬鎓阳离子的形成为关键中间体，主要产物为 1,1,4,4- 四甲氧基环己-2,5-二烯、1,1,4-三甲氧基-4-(偶氮唑-1-基)环己-2,5-二烯和 1,4- 二甲氧基-2-(偶氮唑-1-基)苯。在电解过程中，偶氮唑和溶剂分子作为亲核体进行竞争。研究考虑了这一过程的精细机制。

  DOI：

  10.1007/s11172-005-0380-7

文献信息

• PATCH FOR ANTI-DERMATOPHYTOSIS
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US20150209301A1

  公开（公告）日：2015-07-30

  A patch for nails or skin for prevention or treatment of dermatophytosis, containing a layer including a pressure sensitive adhesive layer and a compound represented by the formula: wherein R 1 represents hydrogen, C 1-16 alkyl, or trifluoromethyl; R 2 represents hydrogen, C 1-6 alkyl, halogen, —COO(C 1-6 alkyl), or (CH 2 ) 1-3 COOR; R 3 represents hydrogen, C 1-6 alkyl, amino, trifluoromethyl, or OR; R 4 represents hydroxyl; R 5 represents hydrogen, C 1-6 alkyl, hydroxyl, or halogen; R 6 represents hydrogen, C 1-6 alkyl, trifluoromethyl, halogen, amino, —NR a R b , nitro, hydroxy-C 1-6 alkyl, —CONR a R b , —COO(C 1-6 alkyl), —COOH, —(CH 2 ) 1-3 COOR, or OR a (R a and R b each represents hydrogen, C 1-6 alkyl, or C 1-6 acyl); R 7 represents hydrogen, C 1-6 alkyl, —OR, or halogen; R 8 represents hydrogen, C 1-6 alkyl, hydroxyl, amino, or nitro; and R represents hydrogen or C 1-6 alkyl; or a salt thereof.

  一种用于预防或治疗皮肤真菌病的指甲或皮肤贴片，包含一个层，其中包括一个压敏粘合剂层和一个由以下式表示的化合物： 其中R 1 代表氢、C 1-16 烷基或三氟甲基；R 2 代表氢、C 1-6 烷基、卤素、—COO(C 1-6 烷基)或(CH 2 ) 1-3 COOR；R 3 代表氢、C 1-6 烷基、氨基、三氟甲基或OR；R 4 代表羟基；R 5 代表氢、C 1-6 烷基、羟基或卤素；R 6 代表氢、C 1-6 烷基、三氟甲基、卤素、氨基、—NR a R b 、硝基、羟基-C 1-6 烷基、—CONR a R b 、—COO(C 1-6 烷基)、—COOH、—(CH 2 ) 1-3 COOR或OR a （R a 和R b 各自代表氢、C 1-6 烷基或C 1-6 酰基）；R 7 代表氢、C 1-6 烷基、—OR或卤素；R 8 代表氢、C 1-6 烷基、羟基、氨基或硝基；R代表氢或C 1-6 烷基；或其盐。
• Arenium cation as the key intermediate of the electrosynthesis of N-(2,5-dimethoxyphenyl)azoles. A new approach to the synthesis of N-(dimethoxyphenyl)azoles
  作者：V. A. Petrosyan、A. V. Burasov

  DOI：10.1007/s11172-007-0342-3

  日期：2007.11

  Data on the effect of the acid-base properties of the medium on the yield and composition of the products of N-dimethoxyphenylation of azoles (pyrazole, triazole, their substituted derivatives, and tetrazole) upon galvanostatic electrolysis of azole—1,4-dimethoxybenzene mixtures in nucleophilic (MeOH) and neutral (MeCN) media were considered and the trends of this process were discussed. The generation of arenium cations (1,4-dimethoxy-1-azolylbenzenium in MeCN and 1,1,4-trimethoxybenzenium in MeOH) as the key intermediates of electrosynthesis of N-(dimethoxyphenyl)azoles, was proved experimentally. A new approach to the synthesis of N-(dimethoxyphenyl)azoles through electrosynthesis of 1,1,4,4-tetramethoxycyclohexa-2,5-diene by electrooxidation of 1,4-dimethoxybenzene in MeOH as the first step and the reaction of this quinone diketal with azoles as the second step was suggested. The efficiency of this route to N-(dimethoxyphenyl)azoles is comparable with the efficiency of the purely electrochemical one-step process.

  关于电解质介质的酸碱性质对氮二甲氧基苯化吡唑、三唑及其取代衍生物和四唑（统称为氮二甲氧基苯化唑类）在电化学恒流电解法制备产物产率和组成的影响的数据在亲核（甲醇）和中性（乙腈）介质中进行了考虑和讨论，并讨论了其过程趋势。通过实验证实了芳铵阳离子（乙腈中的1,4-二甲氧基-1-唑基苯铵和甲醇中的1,1,4-三甲氧基苯铵）作为氮（二甲氧基苯基）唑类电合成关键中间体的生成。提出了通过电合成1,4-二甲氧基苯在甲醇中的电氧化生成1,1,4,4-四甲氧基环己-2,5-二烯作为第一步，以及该醌二酮与唑类反应作为第二步的氮（二甲氧基苯基）唑类合成新途径。此途径的效率与纯电化学一步法相当。
• TOPICAL LIQUID AGENT FOR THE TREATMENT OF DERMATOPHYTOSIS
  申请人：MEIJI SEIKA PHARMA CO., LTD.

  公开号：US20140030209A1

  公开（公告）日：2014-01-30

  A topical liquid agent for a nail and/or skin for prevention or treatment of dermatophytosis comprises a film-forming agent and a compound represented by the formula: wherein R 1 represents hydrogen, C 1-6 alkyl, or trifluoromethyl, R 2 represents hydrogen, C 1-6 alkyl, halogen, —COO(C 1-6 alkyl), or (CH 2 ) 1-3 COOR where R represents hydrogen or C 1-6 alkyl, R 3 represents hydrogen, C 1-6 alkyl, amino, trifluoromethyl, or OR where R represents hydrogen or C 1-6 alkyl, R 4 represents hydroxyl, R 5 represents hydrogen, C 1-6 alkyl, hydroxyl, or halogen, R 6 represents hydrogen, C 1-6 alkyl, trifluoromethyl, halogen, amino, —NR a R b , nitro, hydroxy-C 1-6 alkyl, —CONR a R b , —COO(C 1-6 alkyl), —COOH, —(CH 2 ) 1-3 COOR, or OR a where R represents hydrogen or C 1-6 alkyl, R a and R b each represent hydrogen, C 1-6 alkyl, or C 1-6 acyl, R 7 represents hydrogen, C 1-6 alkyl, —OR where R represents hydrogen or C 1-6 alkyl, or halogen, R 8 represents hydrogen, C 1-6 alkyl, hydroxyl, amino, or nitro, or a salt thereof.

  一种用于预防或治疗真菌感染的指甲和/或皮肤的局部液体剂包括一种成膜剂和一个表示为以下结构式的化合物：其中R1代表氢、C1-6烷基或三氟甲基，R2代表氢、C1-6烷基、卤素、—COO(C1-6烷基)或(CH2)1-3COOR，其中R代表氢或C1-6烷基，R3代表氢、C1-6烷基、氨基、三氟甲基或OR，其中R代表氢或C1-6烷基，R4代表羟基，R5代表氢、C1-6烷基、羟基或卤素，R6代表氢、C1-6烷基、三氟甲基、卤素、氨基、—NRaRb、硝基、羟基-C1-6烷基、—CONRaRb、—COO(C1-6烷基)、—COOH、—(CH2)1-3COOR或ORa，其中R代表氢或C1-6烷基，Ra和Rb分别代表氢、C1-6烷基或C1-6酰基，R7代表氢、C1-6烷基、—OR（其中R代表氢或C1-6烷基）或卤素，R8代表氢、C1-6烷基、羟基、氨基或硝基，或其盐。
• Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene
  作者：V. A. Petrosyan、A. V. Burasov、T. S. Vakhotina

  DOI：10.1007/s11172-005-0380-7

  日期：2005.5

  The reactions of 1,4-dimethoxybenzene with azoles (pyrazole, triazole, and their derivatives, as well as tetrazole) were studied by undivided amperostatic electrolysis at Pt electrodes in MeOH. The process proceeds via the formation of a 1,1,4-trimethoxyarenonium cation as the key intermediate and affords 1,1,4,4-tetramethoxycyclohexa-2,5-diene, 1,1,4-trimethoxy-4-(azol-1-yl)cyclohexa-2,5-diene, and 1,4-dimethoxy-2-(azol-1-yl)benzene as the main products. Azole and solvent molecules compete as nucleophiles during electrolysis. A fine mechanism of the process was considered.

  在 MeOH 中，通过在铂电极上进行不分裂的安培静态电解，研究了 1,4 二甲基苯与偶氮唑（吡唑、三唑及其衍生物以及四唑）的反应。该过程以 1,1,4- 三甲氧基壬鎓阳离子的形成为关键中间体，主要产物为 1,1,4,4- 四甲氧基环己-2,5-二烯、1,1,4-三甲氧基-4-(偶氮唑-1-基)环己-2,5-二烯和 1,4- 二甲氧基-2-(偶氮唑-1-基)苯。在电解过程中，偶氮唑和溶剂分子作为亲核体进行竞争。研究考虑了这一过程的精细机制。
• ANTITRICHOPHYTOSIS SOLUTION FOR EXTERNAL USE
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP2889031A1

  公开（公告）日：2015-07-01

  According to the present invention, a topical liquid agent having antifungal activity against dermatophytes, and further high nail permeability can be provided. The topical liquid agent for nail and/or skin for prevention or treatment of dermatophytosis comprises a film-forming agent and a compound represented by the formula: wherein R1 represents a hydrogen atom, C1-6 alkyl, or trifluoromethyl, R2 represents a hydrogen atom, C1-6 alkyl, halogen, -COO(C1-6 alkyl), or (CH2)1-3COOR where R represents a hydrogen atom or C1-6 alkyl, R3 represents a hydrogen atom, C1-6 alkyl, amino, trifluoromethyl, or OR where R represents a hydrogen atom or C1-6 alkyl, R4 represents a hydroxyl group, R5 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, or halogen, R6 represents a hydrogen atom, C1-6 alkyl, trifluoromethyl, halogen, amino, -NRaRb, nitro, hydroxy-C1-6 alkyl, -CONRaRb, -COO(C1-6 alkyl), -COOH, -(CH2)1-3COOR, or ORa where R represents a hydrogen atom or C1-6 alkyl, Ra and Rb may be the same or different from each other, and each represent a hydrogen atom, C1-6 alkyl, or C1-6 acyl, R7 represents a hydrogen atom, C1-6 alkyl, -OR where R represents a hydrogen atom or C1-6 alkyl, or halogen, R8 represents a hydrogen atom, C1-6 alkyl, a hydroxyl group, amino, or nitro, or a salt thereof.

  根据本发明，可以提供一种对皮癣菌具有抗真菌活性的外用液体制剂，而且该制剂还具有较高的指甲渗透性。 这种用于指甲和/或皮肤、预防或治疗皮癣菌病的外用液体制剂包括一种成膜剂和一种由式表示的化合物： 其中 R1 代表氢原子、C1-6 烷基或三氟甲基，R2 代表氢原子、C1-6 烷基、卤素、-COO(C1-6 烷基)或 (CH2)1-3COOR 其中 R 代表氢原子或 C1-6 烷基，R3 代表氢原子、C1-6 烷基、氨基、三氟甲基或 OR 其中 R 代表氢原子或 C1-6 烷基，R4 代表羟基，R5 代表氢原子、C1-6 烷基、羟基或卤素，R6 代表氢原子、C1-6 烷基、三氟甲基、卤素、-COO(C1-6 烷基)或 (CH2)1-3COOR 其中 R 代表氢原子或 C1-6 烷基、三氟甲基、卤素、氨基、-NRaRb、硝基、羟基-C1-6 烷基、-CONRaRb、-COO(C1-6 烷基)、-COOH、-(CH2)1-3COOR 或 ORa，其中 R 代表氢原子或 C1-6 烷基，Ra 和 Rb 可以相同或不同、R7 代表氢原子、C1-6 烷基、-OR（其中 R 代表氢原子或 C1-6 烷基）或卤素；R8 代表氢原子、C1-6 烷基、羟基、氨基或硝基、 或其盐。