4-(1,4-dioxa-5-oxo-6-heptenyl)-6-methyl-2-pyrone | 136721-19-2

• 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-(1,4-dioxa-5-oxo-6-heptenyl)-6-methyl-2-pyrone
• 英文别名: 2-(2-Methyl-6-oxopyran-4-yl)oxyethyl prop-2-enoate
• CAS: 136721-19-2
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: DEWWRSXKYJNLJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙烯酸氯乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 22.0h， 生成 4-(1,4-dioxa-5-oxo-6-heptenyl)-6-methyl-2-pyrone
  参考文献：
  名称：

  Intramolecular photochemical reactions of 4-(.omega.-alkenyloxy)-6-methyl-2-pyrones having an alkoxycarbonyl group at the olefinic carbon chain

  摘要：

  Photochemical reactions of 4-(omega-alkenyloxy)-6-methyl-2-pyrones 4-8 were investigated. Photosensitized reactions of 2-pyrones 4-6 gave intramolecular [2 + 2] cycloadducts 14-16 as oxatricyclic lactones, site-, regio- and stereospecifically, but 7 and 8 gave no products. On the other hand, direct irradiations of 4 and 5 afforded cyclobutenecarboxylic acids 19 and 20, respectively. The intramolecular cycloaddition mechanism was also explained from the excited state of 2-pyrone calculated by means of the MNDO-CI method.

  DOI：

  10.1021/jo00025a035

文献信息

• Intramolecular photochemical reactions of 4-(.omega.-alkenyloxy)-6-methyl-2-pyrones having an alkoxycarbonyl group at the olefinic carbon chain
  作者：Tetsuro Shimo、Jun Tajima、Takaaki Suishu、Kenichi Somekawa

  DOI：10.1021/jo00025a035

  日期：1991.12

  Photochemical reactions of 4-(omega-alkenyloxy)-6-methyl-2-pyrones 4-8 were investigated. Photosensitized reactions of 2-pyrones 4-6 gave intramolecular [2 + 2] cycloadducts 14-16 as oxatricyclic lactones, site-, regio- and stereospecifically, but 7 and 8 gave no products. On the other hand, direct irradiations of 4 and 5 afforded cyclobutenecarboxylic acids 19 and 20, respectively. The intramolecular cycloaddition mechanism was also explained from the excited state of 2-pyrone calculated by means of the MNDO-CI method.