spiro<(2',6'-dimethylenecyclohexane)-1',2-(5-methylene-1,2,3,4,5,6,7,8-octahydronaphthalene)> | 141805-85-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: spiro<(2',6'-dimethylenecyclohexane)-1',2-(5-methylene-1,2,3,4,5,6,7,8-octahydronaphthalene)>
• 英文别名: 2',4,6'-Trimethylidenespiro[1,2,3,5,6,8-hexahydronaphthalene-7,1'-cyclohexane]
• CAS: 141805-85-8
• 化学式: C₁₈H₂₄
• 分子量: 240.389
• InChiKey: IJOYYEONIDTUQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1,2,3-trimethylenecyclohexane 以 氘代苯 为溶剂， 95.0 ℃ 、1.33 Pa 条件下， 反应 2.5h， 以90%的产率得到spiro<(2',6'-dimethylenecyclohexane)-1',2-(5-methylene-1,2,3,4,5,6,7,8-octahydronaphthalene)>
  参考文献：
  名称：

  Synthesis and dimerization of two cross-conjugated trienes: 3-methylene-1,4-pentadiene and 1,2,3-trimethylenecyclohexane

  摘要：

  3-Methylene-1,4-pentadiene (8) and 1,2,3-trimethylenecyclohexane (10) are prepared in moderate to high yields in good purity by the flash vacuum pyrolysis of 1,5-diacetoxy-3-(acetoxymethyl)pentane (12) and 1,2,3-tris(acetoxymethyl)cyclohexane (17), respectively. Triene 8 dimerizes cleanly at a moderate rate in benzene at 95-degrees-C to give only one major product, [4 + 2] dimer 1,4,4-trivinylcyclohexene (13). Triene 10, the conformationally restricted all cisoid analog of 8, dimerizes more rapidly in benzene at 95-degrees-C to give only one major dimer, a [4 + 2] dimer (21). It is concluded that the dimerization proceeds by a two-step mechanism: rate-determining attack at the middle methylene group to form a resonance-stabilized diradical intermediate followed by rapid closure of the diradical to give a [4 + 2] dimer.

  DOI：

  10.1021/jo00043a032

文献信息

• Synthesis and dimerization of two cross-conjugated trienes: 3-methylene-1,4-pentadiene and 1,2,3-trimethylenecyclohexane
  作者：Walter S. Trahanovsky、Kenneth A. Koeplinger

  DOI：10.1021/jo00043a032

  日期：1992.8

  3-Methylene-1,4-pentadiene (8) and 1,2,3-trimethylenecyclohexane (10) are prepared in moderate to high yields in good purity by the flash vacuum pyrolysis of 1,5-diacetoxy-3-(acetoxymethyl)pentane (12) and 1,2,3-tris(acetoxymethyl)cyclohexane (17), respectively. Triene 8 dimerizes cleanly at a moderate rate in benzene at 95-degrees-C to give only one major product, [4 + 2] dimer 1,4,4-trivinylcyclohexene (13). Triene 10, the conformationally restricted all cisoid analog of 8, dimerizes more rapidly in benzene at 95-degrees-C to give only one major dimer, a [4 + 2] dimer (21). It is concluded that the dimerization proceeds by a two-step mechanism: rate-determining attack at the middle methylene group to form a resonance-stabilized diradical intermediate followed by rapid closure of the diradical to give a [4 + 2] dimer.