2,2-diacetyl-3-benzoyloxirane | 90043-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-diacetyl-3-benzoyloxirane
• 英文别名: 1,1'-(3-Benzoyloxirane-2,2-diyl)di(ethan-1-one)；1-(2-acetyl-3-benzoyloxiran-2-yl)ethanone
• CAS: 90043-63-3
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: CQTKLQFBAVKNHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-methyl-5-phenyl-3-furanyl)ethanone 在 氧气 、 rose bengal 作用下， 以 乙腈 为溶剂， 反应 12.08h， 生成 2,2-diacetyl-3-benzoyloxirane
  参考文献：
  名称：

  Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions

  摘要：

  The photooxygenation of 3-acetyl-5-aryl-2-methylfurans la-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80 degreesC after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00559-2

文献信息

• Photosensitized Oxidation of Furans; IX¹. Methods for the Synthesis of Functionalized Oxiranes
  作者：M. L. Graziano、M. R. Iesce、R. Scarpati

  DOI：10.1055/s-1984-30734

  日期：——
• GRAZIANO, M. L.;IESCE, M. R.;SCARPATI, R., SYNTHESIS, BRD, 1984, N 1, 66-68
  作者：GRAZIANO, M. L.、IESCE, M. R.、SCARPATI, R.

  DOI：——

  日期：——
• Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions
  作者：Satoaki Onitsuka、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1016/s0040-4020(01)00559-2

  日期：2001.7

  The photooxygenation of 3-acetyl-5-aryl-2-methylfurans la-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80 degreesC after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results. (C) 2001 Elsevier Science Ltd. All rights reserved.