2,6-dimethyl-2-phenyl-4H-1,3-dioxin-4-one | 83559-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethyl-2-phenyl-4H-1,3-dioxin-4-one
• 英文别名: 2,6-dimethyl-2-phenyl-[1,3]dioxin-4-one；2,6-Dimethyl-2-phenyl-[1,3]dioxin-4-on；2,6-Dimethyl-2-phenyl-2H,4H-1,3-dioxin-4-one；2,6-dimethyl-2-phenyl-1,3-dioxin-4-one
• CAS: 83559-38-0
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: UQEFKFBMJSKSTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-2-phenyl-4H-1,3-dioxin-4-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 以60%的产率得到6-Bromomethyl-2-methyl-2-phenyl-[1,3]dioxin-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of Spiro Ethers and Spiro Ketals via Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones

  摘要：

  A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1,3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of configuration at the spiro center, via Baeyer-Villager oxidation. The configuration of the spiro center is defined by the facial selectivity at the photocycloaddition step. Two examples of complete stereofacial selectivity were achieved. The unique and important application of the developed sequence was demonstrated in enantioselective synthesis of a less thermodynamically stable spiro ketal 43.

  DOI：

  10.1021/jo970816r
• 作为产物：
  描述：

  双乙烯酮 、 苯乙酮 在 甲基三辛基氯化铵 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以74%的产率得到2,6-dimethyl-2-phenyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Dehmlow, Eckehard V.; Shamout, Abdul Rahman, Liebigs Annalen der Chemie, 1982, # 9, p. 1753 - 1755

  摘要：

  DOI：

文献信息

• Room Temperature Acylketene Formation? 1,3-Dioxin-4-ones via Silver(I) Activation of Phenylthioacetoacetate in the Presence of Ketones
  作者：Aaron E. May、Thomas R. Hoye

  DOI：10.1021/jo101372v

  日期：2010.9.3

  Silver(I) activation of thioacetoacetates in the presence of ketones produces 1,3-dioxin-4-ones. Mechanistic studies addressing the intermediacy of an acylketene intermediate are described.

  在酮的存在下，硫代乙酰乙酸盐的银 (I) 活化产生 1,3-dioxin-4-ones。描述了解决酰基烯酮中间体的中间体的机理研究。
• Tuning Diketodioxinone Reactivity: Biomimetic Synthesis of the Resorcylate Antibiotic Fungal Metabolites <i>ent</i>-W1278A, -B, and -C, Using Iterative Aromatization Reactions
  作者：Ismael Navarro、Christoph Pöverlein、Gerhard Schlingmann、Anthony G. M. Barrett

  DOI：10.1021/jo9015858

  日期：2009.11.6

  The onset temperature of the retro-Diels-Alder reactions of diketo-1,3-dioxin-2-ones to generate alpha,gamma,epsilon-triketo-ketenes was found to be significantly reduced with 2-phenyl substitution. These ketenes, generated at 78 degrees C, were trapped with alcohols to provide resorcylate esters following aromatization by sequential reaction with cesium acetate and trifluoroacetic acid. The methodology was applied iteratively to the total synthesis of the resorcylate antibiotics W1278A, -B, and -C. It is noteworthy that in this process the linking of the monomer units occurs during construction of the aromatic ring.
• The Reactions of Diketene with Ketones¹
  作者：Michael F. Carroll、Alfred R. Bader

  DOI：10.1021/ja01117a076

  日期：1953.11
• Enantioselective Synthesis of Spiro Ethers and Spiro Ketals <i>via</i> Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones
  作者：Nizar Haddad、Igor Rukhman、Zehavit Abramovich

  DOI：10.1021/jo970816r

  日期：1997.10.1

  A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1,3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of configuration at the spiro center, via Baeyer-Villager oxidation. The configuration of the spiro center is defined by the facial selectivity at the photocycloaddition step. Two examples of complete stereofacial selectivity were achieved. The unique and important application of the developed sequence was demonstrated in enantioselective synthesis of a less thermodynamically stable spiro ketal 43.
• Dehmlow, Eckehard V.; Shamout, Abdul Rahman, Liebigs Annalen der Chemie, 1982, # 9, p. 1753 - 1755
  作者：Dehmlow, Eckehard V.、Shamout, Abdul Rahman

  DOI：——

  日期：——