4-methyl-6-(4-methylphenyl)-2H-pyran-2-one | 4422-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methyl-6-(4-methylphenyl)-2H-pyran-2-one
• 英文别名: 4-Methyl-6-(4-tolyl)-2-pyrone；4-methyl-6-(4-methylphenyl)pyran-2-one
• CAS: 4422-61-1
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: VQBWDNAKSWMUIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-6-(4-methylphenyl)-2H-pyran-2-one 生成 3-甲基-5-(4-甲基苯基)-5-氧代戊酸
  参考文献：
  名称：

  Lohaus,G. et al., Chemische Berichte, 1967, vol. 100, # 2, p. 658 - 677

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲苯基乙炔 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (IPr)AgCl 、 二异丙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 40.0~50.0 ℃ 、1.0 MPa 条件下， 反应 28.0h， 生成 (Z)-5-(4-methylbenzylidene)-4-methylfuran-2(5H)-one 、 4-methyl-6-(4-methylphenyl)-2H-pyran-2-one
  参考文献：
  名称：

  SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

  摘要：

  C-C bond forming carboxylation, and cyclization: of trimethyl(2-rnethylenbut-3,7yl)silaile derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the:corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2:furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig-cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.

  DOI：

  10.1021/acs.orglett.5b03023

文献信息

• Process for the preparation of 1-hydroxy-pyridones
  申请人：Hoechst Aktiengesellschaft

  公开号：US03972888A1

  公开（公告）日：1976-08-03

  Method for making 6-substituted-1-hydroxy-2-pyridones, which may also be substituted in one or more of the 3-, 4-, and 5-positions, by reaction of the corresponding 2-pyrone with hydroxylamine or its salts in the presence of imidazole or a 2-aminopyridine which may be mono- or di-methyl substituted.

  制备6-取代-1-羟基-2-吡啶酮的方法，可以在3、4和5位中的一个或多个位置上进行取代，通过将相应的2-吡啶酮与羟胺或其盐在咪唑或2-氨基吡啶的存在下反应，该2-氨基吡啶可以是单甲基或双甲基取代的。
• Lohaus; Dittmar, Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 8 a, p. 1311 - 1316
  作者：Lohaus、Dittmar

  DOI：——

  日期：——
• US3972888A
  申请人：——

  公开号：US3972888A

  公开（公告）日：1976-08-03
• SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives
  作者：Kohei Sekine、Yuta Sadamitsu、Tohru Yamada

  DOI：10.1021/acs.orglett.5b03023

  日期：2015.11.20

  C-C bond forming carboxylation, and cyclization: of trimethyl(2-rnethylenbut-3,7yl)silaile derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the:corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2:furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig-cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
• Lohaus,G. et al., Chemische Berichte, 1967, vol. 100, # 2, p. 658 - 677
  作者：Lohaus,G. et al.

  DOI：——

  日期：——