2-(but-3-enyl)-2-methyl-1,3-dioxin-4-one | 201030-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(but-3-enyl)-2-methyl-1,3-dioxin-4-one
• 英文别名: 2-But-3-enyl-2-methyl-1,3-dioxin-4-one
• CAS: 201030-10-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: SEAADIPBETZJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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-(but-3-enyl)-2-methyl-1,3-dioxin-4-one 以 丙酮 、 乙腈 为溶剂， 生成 (1S,3R,6S,9R)-6-Methyl-7,10-dioxa-tricyclo[4.3.1.0^3,9]decan-8-one
  参考文献：
  名称：

  Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

  摘要：

  1,3-Dioxin-4-one photosubstrates were prepared by condensation of alkenones with ketoesters or formyl Meldrum's Acid. The resulting dioxinones contained enone and alkene chromophores, linked through the ketal carbon of the dioxinone ring. The dioxinones were irradiated and the regiochemistry of the photoproducts was established. Substrates with a two carbon tether gave head to head products, while substrates with a three or four carbon tether gave predominantly head to tail products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10381-1
• 作为产物：
  描述：

  5-已烯-2-酮 、 2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbaldehyde 生成 2-(but-3-enyl)-2-methyl-1,3-dioxin-4-one
  参考文献：
  名称：

  Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

  摘要：

  1,3-Dioxin-4-one photosubstrates were prepared by condensation of alkenones with ketoesters or formyl Meldrum's Acid. The resulting dioxinones contained enone and alkene chromophores, linked through the ketal carbon of the dioxinone ring. The dioxinones were irradiated and the regiochemistry of the photoproducts was established. Substrates with a two carbon tether gave head to head products, while substrates with a three or four carbon tether gave predominantly head to tail products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10381-1

文献信息

• Diastereoselective Addition of Radicals to Chiral 1,3-Dioxin-4-ones
  作者：Heiner Graalfs、Roland Fröhlich、Christian Wolff、Jochen Mattay

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1057::aid-ejoc1057>3.0.co;2-a

  日期：1999.5

  the new spirocyclic compounds 22-27. The 1,3-dioxin-4-ones 32a,b possessing an unsaturated side chain were attacked by radicals at the terminal double bond. In the case of irradiation of 32b in 1,3-dioxolane a cyclization followed the intermolecular addition of a 1,3-dioxolan-2-yl radical and the dispiro compound 36 was formed. However, the formation of dispiro compound 40 required two reaction steps

  研究了自由基向 1,3-二恶英-4-酮 1a,b 和 2a,b 的分子间加成，其中 (-)-薄荷酮作为 2 位手性助剂加入。来自 1,3-二氧戊环、氧杂环戊烷和 2-丙醇的光化学产生的自由基被添加到更多暴露的 a 侧，具有高面部选择性。1,3-二氧戊环-2-基自由基向手性二恶英酮的分子内加成效率较低，并且从α-侧也具有较低的选择性。然而，有可能形成新的螺环化合物 22-27。具有不饱和侧链的 1,3-二恶英-4-ones 32a,b 被末端双键处的自由基攻击。在 32b 在 1,3-二氧戊环中辐照的情况下，在 1,3-二氧戊环-2-基的分子间加成之后发生环化反应，形成二螺环化合物 36。然而，二螺环化合物 40 的形成需要两个反应步骤，从 32b 和溴三氯甲烷的辐照开始。在 C-2 处具有不饱和侧链的非手性 1,3-dioxin-4-one 44 优先在 C-6 处受到 1,3-dioxolan-2-yl