2-烯丙基-2-乙烯基-4-烯酸乙酯 | 42998-21-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-烯丙基-2-乙烯基-4-烯酸乙酯
• 英文名称: ethyl 2-allyl-2-vinylpent-4-enoate
• 英文别名: 2-allyl-2-vinyl-4-pentenoate；Ethyl 2-ethenyl-2-prop-2-enylpent-4-enoate
• CAS: 42998-21-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: GAWQUSXGLDPDDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2-烯丙基-2-乙烯基-4-烯酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 4-(甲硫代)丁酸甲酯
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 反应 1.17h， 生成 2-烯丙基-2-乙烯基-4-烯酸乙酯
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048

文献信息

• Metal-Free Oxyaminations of Alkenes Using Hydroxamic Acids
  作者：Valerie A. Schmidt、Erik J. Alexanian

  DOI：10.1021/ja204255e

  日期：2011.8.3

  A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations

  描述了一种自由基介导的无金属烯烃氧胺化方法。该方法利用烯烃加成中脒氧基自由基的独特反应性，使用简单的偶氮二甲酸二异丙酯 (DIAD) 作为自由基陷阱提供一般的双官能化。该协议利用该过程的分子内性质，在所有情况下提供单一区域异构体。环状烯烃的双官能化提供了使用当前方法无法获得的具有高立体选择性的反式氧胺化产物，补充了顺式选择性氧胺化过程。
• Palladium-catalyzed decarboxylation-carbonylation of allylic carbonates to form .beta.,.gamma.-unsaturated esters
  作者：Jiro Tsuji、Koji Sato、Hiroshi Okumoto

  DOI：10.1021/jo00182a005

  日期：1984.4