2-Oxo-4-(4-phenyl-piperazin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile | 862778-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-Oxo-4-(4-phenyl-piperazin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile
• 英文别名: 6-(4-Methylphenyl)-2-oxo-4-(4-phenylpiperazin-1-yl)pyran-3-carbonitrile；6-(4-methylphenyl)-2-oxo-4-(4-phenylpiperazin-1-yl)pyran-3-carbonitrile
• CAS: 862778-12-9
• 化学式: C₂₃H₂₁N₃O₂
• 分子量: 371.439
• InChiKey: UFOJPFWKZKDVMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Oxo-4-(4-phenyl-piperazin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile 、 4-氟苯基丙酮 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以79%的产率得到3-(4-Fluorophenyl)-2-methyl-4-(4-methylphenyl)-6-(4-phenylpiperazin-1-yl)benzonitrile
  参考文献：
  名称：

  Substituent dependent regioselective synthesis of pyranopyrandiones and 1,2-teraryls from 2H-pyran-2-ones

  摘要：

  The one-pot substituent-directed regioselective synthesis of 1,7-diaryl-2-methyl-4H,5H-pyrano[3,4-c]pyran-4,5-diones 3 as the major and 3,4-diaryl-2-methyl-6-methylsulfanylbenzonitriles 4 as the minor products has been delineated through ring transformation of suitably functionalized 2H-pyran-2-ones 1 with aryl acetones 2. Under similar reaction conditions, 6-aryl-4-sec-amino-2H-pyran-2-ones 5 led, regioselectively, to 3,4-diaryl-2-methyl-6-see-aminobenzonitriles 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.084
• 作为产物：
  描述：

  N-苯基哌嗪 、 4-methylsulfanyl-2-oxo-6-p-tolyl-2H-pyran-3-carbonitrile 以 乙醇 为溶剂， 反应 5.0h， 生成 2-Oxo-4-(4-phenyl-piperazin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  Substituent dependent regioselective synthesis of pyranopyrandiones and 1,2-teraryls from 2H-pyran-2-ones

  摘要：

  The one-pot substituent-directed regioselective synthesis of 1,7-diaryl-2-methyl-4H,5H-pyrano[3,4-c]pyran-4,5-diones 3 as the major and 3,4-diaryl-2-methyl-6-methylsulfanylbenzonitriles 4 as the minor products has been delineated through ring transformation of suitably functionalized 2H-pyran-2-ones 1 with aryl acetones 2. Under similar reaction conditions, 6-aryl-4-sec-amino-2H-pyran-2-ones 5 led, regioselectively, to 3,4-diaryl-2-methyl-6-see-aminobenzonitriles 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.084

文献信息

• Versatile Synthesis of Functionalized Tetrahydroisoquinolines by Ring Transformation of 2H-Pyran-2-ones
  作者：Priyanka B. Kole、Fateh V. Singh

  DOI：10.1071/ch19046

  日期：——

  precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved

  官能化的四氢异喹啉是用于构建许多具有治疗重要性的杂环化合物的便利前体。在本文中，我们已经说明了高度取代的四氢异喹啉的有效的合成由2- ħ经由亲核体-介导的转化环吡喃-2-酮与叔丁基-4-氧代哌啶-1-甲酸叔丁酯，随后通过酸介导的裂解叔-丁氧羰基。具有各种取代基的柔性，可以高收率平稳地获得产物。
• Regioselective synthesis of functionalized naphtho[b]thiophenes through a ‘lactone methodology’
  作者：Manish Dixit、Atul Goel

  DOI：10.1016/j.tetlet.2006.03.081

  日期：2006.5

  Benzo[b]thiophene and its benzannulated derivatives are important classes of compounds due to their unique chemical properties and biosteric relationship with indole. In this letter, we report a convenient route for the synthesis of substituted naphtho[b]thiophenes through a ring transformation reaction of suitably functionalized 2H-pyran-2-ones with 6,7-dihydro-5H-benzothiophene-4-one, in good yields

  苯并[ b ]噻吩及其苯甲环化衍生物由于其独特的化学性质和与吲哚的生物立体关系而成为重要的化合物。在这封信中，我们报告了通过适当官能化的2 H-吡喃-2-酮与6,7-二氢-5 H-苯并噻吩-4-酮的环转化反应，合成取代的萘并[ b ]噻吩的简便方法，收益率很高。
• Ultrasound-Assisted Rapid Synthesis of Functionalized 1,2-Teraryls by Ring Transformation Methodology
  作者：Fateh V. Singh、Manjula Krishnan

  DOI：10.1055/a-1856-1905

  日期：2022.12

  The function of styryl acetate as a carbanion nucleophile source has been explored in the ring transformation reaction of 2H-pyranones. The ultrasound-assisted carbanion-induced ring transformation of 4-amino-6-aryl-3-cyano-2H-pyran-2-ones using (E)-styryl acetate in the presence of KOH and DMF at room temperature is presented as an alternative strategy for the synthesis of functionalized 1,2-teraryls

  在 2 H-吡喃酮的环转化反应中探索了乙酸苯乙烯基酯作为碳负离子亲核试剂源的功能。超声辅助碳负离子诱导的 4-氨基-6-芳基-3-氰基-2 H-吡喃-2-酮的环转变使用 ( E)-苯乙烯基乙酸酯在 KOH 和 DMF 存在下在室温下作为高产率合成功能化 1,2-四芳基化合物的替代策略提出。这种无金属方法可以轻松获得一系列 1,2-四芳基化合物，并具有广泛的官能团耐受性和温和的反应条件。4-(哌啶-1-基)-6-(噻吩-2-基)-[1,1'-联苯]-3-腈的单晶X射线衍射分析表明该晶体属于单斜晶系P21 空间群具有扭曲的芳环。