9,10,10-tetramethyl-11-oxatricyclo[6.3.0.0^1,7]undec-2-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 9,10,10-tetramethyl-11-oxatricyclo[6.3.0.0^1,7]undec-2-ene
• 英文别名: (1S,7R,8S)-9,9,10,10-tetramethyl-11-oxatricyclo[5.4.0.01,8]undec-2-ene
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: VMYCPFXXEYMNBZ-SUNKGSAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 cis,cis-2,7-cyclooctadienone 以 正己烷 为溶剂， 反应 14.0h， 以33%的产率得到9,10,10-tetramethyl-11-oxatricyclo[6.3.0.0^1,7]undec-2-ene
  参考文献：
  名称：

  First Example of an Enone−Alkene [2 + 2 + 2] Photocycloaddition:  1,3-Photocycloaddition of Tetramethylethylene across 2,7-Cyclooctadienone

  摘要：

  [GRAPHICS]Irradiation of cyclooctadienone (1) in the presence of tetramethylethylene (TME) produces 9,10,10-tetramethyl-11 oxatricyclo[6.3.0.0(1,7)]undec-2- ene (7) in 33% yield, This reaction is the first example of a 1,3-cycloaddition of an alkene across an enone system. This novel cycloaddition suggests that there is substantial interaction between the carbonyl carbon and the beta-enone carbon in the triplet excited state of 1.

  DOI：

  10.1021/ol990055+

文献信息

• First Example of an Enone−Alkene [2 + 2 + 2] Photocycloaddition:  1,3-Photocycloaddition of Tetramethylethylene across 2,7-Cyclooctadienone
  作者：Albert R. Matlin、Susanne C. Lin、Hiren R. Patel、Minghui Chai

  DOI：10.1021/ol990055+

  日期：1999.7.1

  [GRAPHICS]Irradiation of cyclooctadienone (1) in the presence of tetramethylethylene (TME) produces 9,10,10-tetramethyl-11 oxatricyclo[6.3.0.0(1,7)]undec-2- ene (7) in 33% yield, This reaction is the first example of a 1,3-cycloaddition of an alkene across an enone system. This novel cycloaddition suggests that there is substantial interaction between the carbonyl carbon and the beta-enone carbon in the triplet excited state of 1.