(3E,8E)-2,9-Dimethyl-1,3,8,10-undecatetraene

• 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,8E)-2,9-Dimethyl-1,3,8,10-undecatetraene
• 英文别名: (3E,8E)-2,9-dimethylundeca-1,3,8,10-tetraene
• 化学式: C₁₃H₂₀
• 分子量: 176.302
• InChiKey: WLAQNYDXCJOIOC-HATNNVTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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,8E)-2,9-Dimethyl-1,3,8,10-undecatetraene 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到<3aR*,7R*,7aR*>-4-Methyl-7-(1-methylethenyl)-2,3,3a,6,7,7a-hexahydro-1H-indene
  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

文献信息

• Influence of Alkyl Substitution on the Intramolecular Ionic Diels-Alder Reaction of Tetraenes
  作者：David B. Gorman、Paul G. Gassman

  DOI：10.1021/jo00109a032

  日期：1995.2

  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.