2,4-二氢-4-[(5-羟基-3-甲基-1-苯基-1H-吡唑-4基)亚甲基]-5-甲基-2-苯基-3H-吡唑-3-酮 | 61466-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2,4-二氢-4-[(5-羟基-3-甲基-1-苯基-1H-吡唑-4基)亚甲基]-5-甲基-2-苯基-3H-吡唑-3-酮
• 英文名称: 4-[(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 4,4-methine-bis-(3-methyl-1-phenyl-2-pyrazolin-5-one)；4,4'-methylidenebis(1-phenyl-3-methylpyrazol-5-one)；4,4'-methylidenebis(3-methyl-1-phenyl-5-pyrazolone)；4,4-methylidenebis(1-phenyl-3-methylpyrazol-5-one)；5,5'-dimethyl-2,2'-diphenyl-1,2,2',4'-tetrahydro-4,4'methanylylidene-bis-pyrazol-3-one；MBP-H；5-Oxo-3-methyl-1-phenyl-4-<5-oxo-3-methyl-1-phenyl-4,5-dihydro-pyrazolidenmethyl>-4,5-dihydro-pyrazol
• CAS: 61466-03-3；4174-09-8
• 化学式: C₂₁H₁₈N₄O₂
• mdl: MFCD00604704
• 分子量: 358.4
• InChiKey: PHCPNSHHXUOXSD-UHFFFAOYSA-N

物化性质

• 熔点：
  320-322 °C
• 沸点：
  547.3±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.72
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三甲基铝 、 2,4-二氢-4-[(5-羟基-3-甲基-1-苯基-1H-吡唑-4基)亚甲基]-5-甲基-2-苯基-3H-吡唑-3-酮 以 甲苯 为溶剂， 以80%的产率得到dimethyl(4,4'-methylidenebis(1-phenyl-3-methylpyrazol-5-one)aluminum
  参考文献：
  名称：

  4-亚甲基-双（1-苯基-3-甲基吡唑-5-酮）与三甲基铝的反应：ε-己内酯开环聚合的合成、结构和催化

  摘要：

  摘要 合成了带有配体O,O-二齿二吡唑酯的铝配合物并对其进行了结构表征。4-亚甲基-双(1-苯基-3-甲基吡唑-5-酮) (MBP-H) 与 AlMe3（1.2 摩尔当量）在甲苯中反应生成 [(MBP)AlMe2] (1) 作为四配位单体铝络合物。三加合物复合物 [Al(MBP)3] (2) 由在甲苯中用 MBP-H（3 摩尔当量）以高产率处理 AlMe3 产生。在 9-蒽甲醇存在下，单加合物铝配合物 1 以受控方式有效催化ε-己内酯 (e-CL) 的开环聚合，产生具有预期分子量和窄多分散指数 (PDI) 的 PCL。

  DOI：

  10.1016/j.inoche.2010.11.012
• 作为产物：
  描述：

  4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl)quinazoline 在 水 作用下， 以 正丁醇 为溶剂， 反应 15.0h， 以14%的产率得到2,4-二氢-4-[(5-羟基-3-甲基-1-苯基-1H-吡唑-4基)亚甲基]-5-甲基-2-苯基-3H-吡唑-3-酮
  参考文献：
  名称：

  Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles

  摘要：

  Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating I with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-5-one reacts with 1 without acid catalysis to form dipyrazolylmethane 6. 4-Chloroquinazoline 8 reacts with 1-phenyl-3-methylpyrazol-5-one to form 4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl) quinazoline 9 and dipyrazolylmethane 6. Heating 8 with 2-methylindole leads to the formation of 4-(2-methylindol-3-yl) quinazoline 10 and tris(2-methylindol-3-yl)methane 11. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.199

文献信息

• Straightforward synthesis of diverse dipyrazolylmethane derivatives and their application for fluorescence sensing of Cu²⁺ ions
  作者：Kaliappan Kaliraj、Likai Xia、Thomas Nesakumar Jebakumar Immanuel Edison、Yong Rok Lee

  DOI：10.1039/c6ra10530k

  日期：——

  A variety of dipyrazolylmethane derivatives were synthesized from the reactions of readily available β-keto esters with arylhydrazine hydrochlorides and DMF in the presence of p-toluenesulfonic acid (p-TsOH). This methodology provides a concise and practical one-pot route for the construction of diverse dipyrazolylmethane derivatives in good yield. As an application, the synthesized nitro-substituted

  在对甲苯磺酸（p- TsOH）存在下，由易得的β-酮酯与芳基肼盐酸盐和DMF反应合成了多种二吡唑基甲烷衍生物。该方法为高产率地构建各种二吡唑基甲烷衍生物提供了一种简明实用的一锅法。作为一种应用，合成的硝基取代的化合物在检测Cu 2+离子方面表现出优异的熄灭荧光传感特性。
• New Synthetic Potential of Pteridine Derivatives: Direct Substitution of H in 1,3-Dimethyllumazine During Reaction with C-Nucleophiles
  作者：Yu. A. Azev、O. S. Ermakova、A. M. Gibor、M. A. Ezhikova、M. I. Kodess、O. N. Chupakhin

  DOI：10.1007/s10600-016-1650-3

  日期：2016.3

  substitution of H in unsubstituted 1,3-dimethyllumazine was reported for the reaction with alkylamines in the presence of oxidizers to give 7-substituted 1,3-dimethyl-2,4-dioxopyrimido-[4,5-b]pyrazine derivatives [4]. The C-6 atom of 1,3-dimethyllumazine was alkoxylated regioselectively during the reaction with N-bromosuccinimide in alcohols [5]. Examples of direct functionalization of C–H bonds using C-nucleophiles

  蝶啶核是用于大量重要的天然和合成生物活性化合物的杂环支架。许多天然蝶啶参与细胞代谢。因此，具有潜在生物活性的新型蝶啶衍生物的区域选择性合成极为重要[1]。在开发天然和合成生物活性杂环化合物的有效合成方法的过程中，通过 C-亲核试剂直接取代 H 并生产具有 C-C 键的产品，使用 C-H 键的 SN H-官能化 [2, 3] . 据报道，在氧化剂存在下与烷基胺反应，在未取代的 1,3-二甲基咪嗪中发生 Chichibabin 取代 H，得到 7-取代的 1,3-二甲基-2,4-二氧嘧啶-[4,5-b] 吡嗪衍生物。 4]。1的C-6原子，在与醇中的 N-溴代琥珀酰亚胺反应期间，3-二甲基噻嗪被区域选择性地烷氧基化 [5]。使用 C-亲核试剂直接官能化 C-H 键的例子对于 1,3-二甲基lumazine 是未知的。本工作的目标是研究 1,3-二甲基联氨嗪与 C-亲核试剂反应中直接 H 取代的
• Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions
  作者：Zeba N. Siddiqui、Kulsum Khan

  DOI：10.1039/c3nj00069a

  日期：——

  Efficient synthesis of benzopyrano[4,3-b]pyridine derivatives was achieved from 4-amino-3-formylcoumarin and different active methylene compounds under solvent-free thermal heating at 80 °C via Friedlander condensation in the presence of chitosan as heterogeneous, basic green catalyst. The present methodology is a novel green approach to benzopyranopyridine. It offers several advantages such as shorter

  高效合成苯并吡喃并[4,3- b ]吡啶衍生物4-氨基-3-甲酰基香豆素在不存在溶剂的情况下，在80°C下通过Friedlander缩合在无溶剂的条件下进行加热加热，得到不同的活性亚甲基化合物壳聚糖作为非均质碱性绿色催化剂。本方法学是一种新颖的绿色方法苯并吡喃吡啶。它具有许多优点，例如反应时间短，反应条件温和，操作程序简单，使用可回收和可生物降解的催化剂。
• New investigation of Vilsmeier-type reaction using pyrazolones with various amides
  作者：Yu-Ying Huang、Kimiyoshi Kaneko、Hiroyuki Takayama、Masayuki Kimura、Fung Fuh Wong

  DOI：10.1016/j.tetlet.2011.05.055

  日期：2011.7

  New investigation of Vilsmeier-type reaction was evaluated to realize the solvent effect by using pyrazolones to react with various of amides, including formamide, N-methylformamide, N-propylformamide, N-tert-butylformamide, N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dipropylformamide (DPF), N,N-diisopropylformamide, N,N-dibutylformamide, piperidine-l-carbaldehyde, and pyrrolidine-l-carbaldehyde, in the presence of phosphorous oxychloride POCl3. The unexpected resulting products were observed in this work according to the difference chemoseletivities of substituted amides. The plausible reactive pathways were proposed to explain the experimental result. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• ——
  作者：Yu. A. Azev、S. V. Shorshnev、D. Gabel

  DOI：10.1023/a:1019686412555

  日期：——