(+/-)-trans-Penten-(3)-yl-(2)-vinylaether | 100961-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-trans-Penten-(3)-yl-(2)-vinylaether
• 英文别名: 4-vinyloxy-pent-2t-ene；(E)-4-ethenoxypent-2-ene
• CAS: 100961-00-0
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: PJJJSPBDXSGONK-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-Penten-(3)-yl-(2)-vinylaether 反应 0.5h， 生成 3-methyl-4-hexenal
  参考文献：
  名称：

  串联Pd（II）催化的乙烯基醚交换-克莱森重排作为γ，δ-不饱和醛的简便方法

  摘要：

  报道了钯（II）-菲咯啉配合物催化的烯丙基乙烯基醚的顺序形成-克莱森重排过程。讨论了烯丙醇结构，乙烯基化剂类型和钯催化剂的影响。该方法提供了一种在温和条件下避免使用有毒的Hg（II）催化剂的γ，δ-不饱和醛的简便方法。新方法已经成功地在千克规模上得到了证明。

  DOI：

  10.1021/jo062548f
• 作为产物：
  描述：

  3-penten-2-ol 、 乙烯基乙醚 在 mercury(II) diacetate 作用下， 生成 (+/-)-trans-Penten-(3)-yl-(2)-vinylaether
  参考文献：
  名称：

  The Steric Course of the Claisen Rearrangement

  摘要：

  An infrared study of the stereochemistry attending the Claisen rearrangement of cis- and trans-alpha,gamma-dimethylallyl and two other related vinyl ethers has shown that the reaction produces essentially only trans substituted allylacetaidehydes. The double bond in the o-Claisen rearrangement product of trans-alpha, gamma-dimethylallyl phenyl ether has also been demonstrated by infrared absorption to be predominantly trans. The transition state geometry of the Claisen rearrangement implied by these findings is discussed.

  DOI：

  10.1021/ja01502a057

文献信息

• Efficient assembly of α-methylene-γ-butyrolactones via a novel, tandem Claisen–ene rearrangement
  作者：Cédric Leclercq、István E. Markó

  DOI：10.1016/j.tetlet.2005.08.065

  日期：2005.10

  A novel method for the rapid assembly of alpha-methylene-gamma-butyrolactones, using a tandem Claisen-ene rearrangement as a key step, is presented. The importance of the structure of the Lewis acid promoters and the mechanism of action of Et2AlSPh are discussed. (c) 2005 Elsevier Ltd. All rights reserved.
• Tandem Pd(II)-Catalyzed Vinyl Ether Exchange−Claisen Rearrangement as a Facile Approach to γ,δ-Unsaturated Aldehydes
  作者：Xudong Wei、Jon C. Lorenz、Suresh Kapadia、Anjan Saha、Nizar Haddad、Carl A. Busacca、Chris H. Senanayake

  DOI：10.1021/jo062548f

  日期：2007.5.1

  A sequential allyl vinyl ether formation−Claisen rearrangement process catalyzed by a palladium(II)−phenanthroline complex is reported. The effects of allylic alcohol structure, type of vinylating agent, and palladium catalysts are discussed. This method provides a convenient approach to γ,δ-unsaturated aldehydes under mild conditions that avoid the use of toxic Hg(II) catalysts. The new methodology

  报道了钯（II）-菲咯啉配合物催化的烯丙基乙烯基醚的顺序形成-克莱森重排过程。讨论了烯丙醇结构，乙烯基化剂类型和钯催化剂的影响。该方法提供了一种在温和条件下避免使用有毒的Hg（II）催化剂的γ，δ-不饱和醛的简便方法。新方法已经成功地在千克规模上得到了证明。
• The Steric Course of the Claisen Rearrangement
  作者：Albert W. Burgstahler

  DOI：10.1021/ja01502a057

  日期：1960.9

  An infrared study of the stereochemistry attending the Claisen rearrangement of cis- and trans-alpha,gamma-dimethylallyl and two other related vinyl ethers has shown that the reaction produces essentially only trans substituted allylacetaidehydes. The double bond in the o-Claisen rearrangement product of trans-alpha, gamma-dimethylallyl phenyl ether has also been demonstrated by infrared absorption to be predominantly trans. The transition state geometry of the Claisen rearrangement implied by these findings is discussed.