(E)-4,6-heptadien-2-yl 2-propenoate | 491847-08-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-4,6-heptadien-2-yl 2-propenoate
• 英文别名: [(4E)-hepta-4,6-dien-2-yl] prop-2-enoate
• CAS: 491847-08-6
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ODWUDVQXQOKFSM-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4,6-heptadien-2-yl 2-propenoate 在 正丁基锂 、 三氟甲磺酰胺 、 RhCl(PPh₃)3 、 氢气 、 二甲基氯化铝 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 15.0h， 生成 (3S*,4aR*,8aS*)-3,8a-dimethyloctahydroisochromen-1-one
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Tethered 1,7,9-Decatrienoates:  Bis[chloro(methyl)aluminum]trifluoromethanesulfonamide as a Catalyst

  摘要：

  The intramolecular Diels-Alder reaction of 1,7,9-decatrienoate derivative with an ester tether is efficiently catalyzed by the bidentate Lewis acid,/bis-aluminated trifluoromethanesulfonamide.

  DOI：

  10.1021/ol026963f
• 作为产物：
  描述：

  丙烯酰氯 、 (E)-4,6-heptadienyl-2-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到(E)-4,6-heptadien-2-yl 2-propenoate
  参考文献：
  名称：

  Intramolecular Diels−Alder Reactions of Ester-Tethered 1,7,9-Decatrienoates:  Bis[chloro(methyl)aluminum]trifluoromethanesulfonamide as a Catalyst

  摘要：

  The intramolecular Diels-Alder reaction of 1,7,9-decatrienoate derivative with an ester tether is efficiently catalyzed by the bidentate Lewis acid,/bis-aluminated trifluoromethanesulfonamide.

  DOI：

  10.1021/ol026963f

文献信息

• Intramolecular Diels–Alder reaction of 1,7,9-decatrienoates catalyzed by indium(III) trifluoromethanesulfonate in aqueous media
  作者：Hikaru Yanai、Akio Saito、Takeo Taguchi

  DOI：10.1016/j.tet.2005.05.062

  日期：2005.7

  The intramolecular Diels–Alder reaction of ester-tethered 1,7,9-decatrienoate derivatives in a mixture of water and 2-propanol was catalyzed by indium(III) triflate to give the cycloadducts in good yield with perfect endo-selectivity.

  三氟甲磺酸铟（III）催化酯键合的1,7,9-癸三烯酸酯衍生物在水和2-丙醇混合物中的分子内Diels-Alder反应，从而以良好的收率和完美的内选择性使环加合物生成。
• Efficient intramolecular Diels–Alder reactions of ester-tethered 1,7,9-decatrienoates catalyzed by bis-aluminated trifluoromethanesulfonamide
  作者：Akio Saito、Hikaru Yanai、Takeo Taguchi

  DOI：10.1016/j.tet.2004.10.012

  日期：2004.12

  Bis-aluminated trifluoromethanesulfonamide generated in situ by mixing TfNH2 (1 mol) and methylaluminum reagent (2 mol) is an effective catalyst for the IMDA reaction of ester-tethered 1,7,9-decatrienoates. (C) 2004 Elsevier Ltd. All rights reserved.
• Development of effective Lewis acids for the catalytic Diels–Alder reaction of α,β-unsaturated lactones with cyclopentadiene
  作者：Hikaru Yanai、Arata Takahashi、Takeo Taguchi

  DOI：10.1016/j.tetlet.2007.02.131

  日期：2007.4

  We found that 'Tf2CH2 + Me3Al' systems are effective catalytic systems for the DA reaction of less reactive alpha,beta-unsaturated lactone derivatives, compared to alpha,beta,-unsaturated ester derivatives, with cyclopentadiene. Mononuclear aluminum methide complex, Tf2CHAlMe2, as an active species is formed in these catalytic systems. Effects of lactone ring-size on the reactivity and stereoselectivity were also examined. By expanding ring-size, reactivity of alpha,beta-unsaturated lactones reduced but endo-selectivity notably increased. (c) 2007 Elsevier Ltd. All rights reserved.