(3E,9E)-2,11-Dimethyl-1,3,9,11-dodecatetraene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (3E,9E)-2,11-Dimethyl-1,3,9,11-dodecatetraene
• 英文别名: (3E,9E)-2,11-dimethyldodeca-1,3,9,11-tetraene
• 化学式: C₁₄H₂₂
• 分子量: 190.329
• InChiKey: FWNYNOYNVNIUNR-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3E,9E)-2,11-Dimethyl-1,3,9,11-dodecatetraene 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以10%的产率得到<4aR*,8R*,8aS*>-1,2,3,4,4a,7,8,8a-Octahydro-6-methyl-8-(1-methylethenyl)naphthalene
  参考文献：
  名称：

  Influence of Alkyl Substitution on the Intramolecular Ionic Diels-Alder Reaction of Tetraenes

  摘要：

  Fifteen tetraenes, comprised primarily of methylated analogs of (3E,8E)-1,3,8,10-undecatetraene, were synthesized and treated with acid to study the influence of alkyl substitution on the intramolecular ionic Diels-Alder reaction. Depending on methyl substitution patterns of these tetraenes, bicyclo[4.3.0]nonyl, bicyclo[4.4.0]decyl, and bicyclo[5.4.0]undecyl ring systems were produced. For two tetraenes, the ring preference between two different Diels-Alder-derived ring skeletons could be controlled using different temperatures and acid catalysts. Mechanistically, a stepwise process was postulated for at least some of these Diels-Alder reactions. The irreversible and stereoselective formation of the same Diels-Alder product from two noninterconverting tetraenes, which differed only by the cis-trans relationship of a terminal methyl group, was best explained by a stepwise process. A stepwise process was best demonstrated when intermediate triene products isolated from a reaction mixture irreversibly cyclized to Diels-Alder products when resubmitted to the reaction conditions. Although several of the tetraenes failed to give significant amounts of Diels-Alder products, certain alkyl substitution patterns were identified which generally led to high yields of cyclized products.

  DOI：

  10.1021/jo00109a032