2-(4-methylphenyl)-6-methyl-4H-pyran-4-one | 1173000-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(4-methylphenyl)-6-methyl-4H-pyran-4-one
• 英文别名: 2-methyl-6-(4-methylphenyl)-4H-pyran-4-one
• CAS: 1173000-80-0
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: QSZXVGRGLCTCBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-6-methyl-4H-pyran-4-one 在 氯磺酸 作用下， 反应 6.27h， 生成 2-[3-(N,N-di-ethylaminosulfonyl)-4-methylphenyl]-6-methyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of Mono- and Bis-chlorosulfonylarylpyrones and Related Sulfonates and Sulfonamides

  摘要：

  New 2,6-bis[(3-chlorosulfonyl-4-methyl)phenyl]-4H-pyran-4-one and 2-[(3-chlorosulfonyl-4-methyl)phenyl]-6-methyl-4H-pyran-4-one were synthesized by means of a reaction of chlorosulfonic acid with corresponding pyrones at 050 degrees C and were treated with various alcohols and primary and secondary alkyl and aryl amines to give the corresponding sulfonates 4a-e in 20-49% and sulfonamides 3a-l in 55-82% yields. GRAPHICAL ABSTRACT[image omitted].

  DOI：

  10.1080/10426507.2010.484904
• 作为产物：
  描述：

  在 硫酸 作用下， 生成 2-(4-methylphenyl)-6-methyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of Novel Imidazolium and Benzimidazolium Salts from Halomethyl Derivatives of 4-Pyrones

  摘要：

  通过对 4H-吡喃-4-酮的卤代甲基衍生物进行各种季铵化反应，合成了一系列 4-吡喃酮衍生物的单苯并咪唑盐和双苯并咪唑盐以及咪唑盐，产率良好。这些盐可用作功能化 N-杂环碳烯的新型前体，其中一些还可用作新型离子液体。

  DOI：

  10.2174/157017812803521153

文献信息

• Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides
  作者：Aziz Shahrisa、Mahnaz Saraei

  DOI：10.1002/jhet.79

  日期：2009.3

  Hexaminium salts of 4-pyrones were synthesized by treatment of 2-(4-bromomethylphenyl)-6-methyl-4H-pyran-4-one and 2-(4-bromomethylphenyl)-6-phenyl-4H-pyran-4-one with hexamethyl-enetetramine in chloroform in 71 and 84% yields respectively. Hydrolysis of and in EtOH:H2O produced the corresponding aldehydes and in 43 and 58% yields respectively. The reaction of bromopyrones and with dimethylsulfide

  4-吡喃六甲铵盐 通过处理合成 2-（4-溴甲基苯基）-6-甲基-4 H-吡喃-4-酮 和 2-（4-溴甲基苯基）-6-苯基-4 H-吡喃-4-酮 和 六甲基-亚乙基四胺在氯仿中的产率分别为71％和84％。水解的 和 在EtOH：H 2 O中产生相应的醛 和 分别有43％和58％的产量。溴吡喃酮的反应 和 和 甲醇中的二甲基硫醚：CH 2 Cl 2提供相应的sulf盐 和 分别有66％和65％的产量。治疗 和 与芳烃carbaldehydes如（AR = p -ClC 6 ħ 4，ö -ClC 6 ħ 4，p -NO 2 ç 6 ħ 4，ö -NO 2 ç 6 ħ 4，p -FC 6 ħ 4，2-萘基，p -MeOC 6 H 4，C 6 H 5 CH CH，p -MeC 6 H 4，C 6 H 5和4-（4-氧代-6-苯基-4 H-吡喃-2-基）苯甲醛 ）在CH 3 CN：H 2 O中存在
• Synthesis of 2,6-bis(1<i>H</i>-indole-6-yl)-4<i>H</i>-pyran-4-ones<i>via</i>Leimgruber-Batcho indole synthesis
  作者：Aziz Shahrisa、Zarrin Ghasemi、Mahnaz Saraei

  DOI：10.1002/jhet.80

  日期：2009.3

  2,6-Bis(1H-indole-6-yl)-4H-pyran-4-one was synthesized via Leimgruber–Batcho methodology starting from 2,6-bis(4-methyl-3-nitrophenyl)-4H-pyran-4-one . Enamine intermediate in this reaction, , reacts with aroyl chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane in dioxane to give the substituted enamines . Enamines undergo reductive cyclization with Fe/AcOH to the corresponding 3-aroylindoles

  2,6-双（1 H-吲哚-6-基）-4 H-吡喃-4-酮 是通过Leimgruber–Batcho方法合成的，从2,6-双（4-甲基-3-硝基苯基）-4 H-吡喃-4-酮 。在该反应中烯化中间体，在存在下，与芳酰氯反应 1,4-二氮杂双环[2.2.2]辛烷在二恶烷生成取代的烯胺。烯胺经历与Fe / AcOH的还原环化反应，生成相应的3-芳基吲哚10a，10b。杂环化学杂志，46，273（2009）。
• Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties
  作者：Aziz Shahrisa、Kazem Dindar Safa、Somayeh Esmati

  DOI：10.1016/j.saa.2013.09.056

  日期：2014.1

  A series of novel imidazo[1,2-a]pyridines possessing 4-pyrone ring were synthesized by three-component condensation of 4-pyrone carbaldehydes, 2-aminopyridines and isocyanides. Bismuth (III) chloride was used as a catalyst in these reactions and desired products were synthesized in good yields at a very short period of time under solvent free conditions. UV-Vis absorption and fluorescence emission spectra of these compounds were investigated. It shown that two of these compounds (10f and 10g) exhibit intense fluorescence in dichloromethane. Optimized ground-state molecular geometries and orbital distributions of these two fluorescent dyes were obtained using density functional theory (DFT). Thermogravimetric analysis and electrochemical properties of these compounds were also studied. (C) 2013 Published by Elsevier B.V.