ethyl 12-methyl-10-oxo-2,11-dioxatricyclo<7.4.0.0^1,7>tridec-12-ene-endo-8-carboxylate | 136721-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 12-methyl-10-oxo-2,11-dioxatricyclo<7.4.0.0^1,7>tridec-12-ene-endo-8-carboxylate
• 英文别名: ethyl 12-methyl-10-oxo-2,11-dioxatricyclo[7.4.0.0^1,7]tridec-12-ene-endo-8-carboxylate；ethyl (1R,6S,7S,8S)-3-methyl-5-oxo-4,13-dioxatricyclo[6.5.0.01,6]tridec-2-ene-7-carboxylate
• CAS: 136721-31-8
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: PKEKJZYNOZZYHZ-OHTBPHCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-(2-methyl-6-oxopyran-4-yl)oxypentanal 在 二苯甲酮 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.0h， 生成 ethyl 12-methyl-10-oxo-2,11-dioxatricyclo<7.4.0.0^1,7>tridec-12-ene-endo-8-carboxylate
  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