4-methyl-6-tert-butyl-2-pyranone | 82343-53-1

• 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-tert-butyl-2-pyranone
• 英文别名: 6-tert-butyl-4-methyl-2H-pyran-2-one；6-tert-butyl-4-methylpyran-2-one
• CAS: 82343-53-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: SIAXJAZJFHRGPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 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， 50.0 ℃ 、1.0 MPa 条件下， 反应 28.0h， 生成 (Z)-5-(2,2-dimethylpropylidene)-4-methylfuran-2(5H)-one 、 4-methyl-6-tert-butyl-2-pyranone
  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

• Selective .gamma.-substitution of .alpha.,.beta.-unsaturated esters via .alpha.-trimethylsilyl .beta.,.gamma.-unsaturated esters
  作者：Pamela Albaugh-Robertson、John A. Katzenellenbogen

  DOI：10.1021/jo00174a026

  日期：1983.12
• Silicon-directed selective gamma substitution of an α,β-unsaturated ester
  作者：Pamela Albaugh-Robertson、John A. Katzenellenbogen

  DOI：10.1016/s0040-4039(00)86931-2

  日期：1982.1
• ALBAUGH-ROBERTSON, P.;KATZENELLENBOGEN, J. A., TETRAHEDRON LETT., 1982, 23, N 7, 723-726
  作者：ALBAUGH-ROBERTSON, P.、KATZENELLENBOGEN, J. A.

  DOI：——

  日期：——
• ALBAUGH-ROBERTSON, P.;KATZENELLENBOGEN, J. A., J. ORG. CHEM., 1983, 48, N 26, 5288-5302
  作者：ALBAUGH-ROBERTSON, P.、KATZENELLENBOGEN, J. A.

  DOI：——

  日期：——
• 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.