(1E)-1-(1,3-Dimethyl-2-butenylidene)-2-(2-methyl-1-propenyl)cyclopentane | 130380-02-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (1E)-1-(1,3-Dimethyl-2-butenylidene)-2-(2-methyl-1-propenyl)cyclopentane
• 英文别名: (1E)-1-(4-methylpent-3-en-2-ylidene)-2-(2-methylprop-1-enyl)cyclopentane
• CAS: 130380-02-8
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: VHTSZHKMFBOYQS-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (1E)-1-(1,3-Dimethyl-2-butenylidene)-2-(2-methyl-1-propenyl)cyclopentane 、 对甲苯磺酸 、 二氯甲烷 生成 5,5,7-trimethyl-4-prop-1-en-2-yl-1,2,3,3a,4,7a-hexahydroindene
  参考文献：
  名称：

  GASSMAN, PAUL G.;GORMAN, DAVID B., J. AMER. CHEM. SOC., 112,(1990) N3, C. 8624-8626

  摘要：

  DOI：
• 作为产物：
  描述：

  (3E,8E)-2,9,11-Trimethyl-1,3,8,10-dodecatetraene 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 <3aR*,7R*,7aS*>-4,6,6-Trimethyl-7-(1-methylethenyl)-2,3,3a,6,7,7a-hexahydro-1H-indene 、 <3aS*,7R*,7aS*>-4,6,6-Trimethyl-7-(1-methylethenyl)-2,3,3a,6,7,7a-hexahydro-1H-indene 、 (1Z)-1-(1,3-Dimethyl-2-butenylidene)-2-(2-methyl-1-propenyl)cyclopentane 、 (1E)-1-(1,3-Dimethyl-2-butenylidene)-2-(2-methyl-1-propenyl)cyclopentane
  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

• Gassman, Paul G.; Gorman, David B., Journal of the American Chemical Society, <hi>1990</hi>, vol. 112, # 23, p. 8624 - 8626
  作者：Gassman, Paul G.、Gorman, David B.

  DOI：——

  日期：——