β-(trifluoromethyl)-β-ethoxy-4-methoxystrene | 141708-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: β-(trifluoromethyl)-β-ethoxy-4-methoxystrene
• 英文别名: 1-[(Z)-2-ethoxy-3,3,3-trifluoroprop-1-enyl]-4-methoxybenzene
• CAS: 141708-79-4
• 化学式: C₁₂H₁₃F₃O₂
• 分子量: 246.229
• InChiKey: OGYYAQFYUMTMQX-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-(trifluoromethyl)-β-ethoxy-4-methoxystrene 、 二苄胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以73%的产率得到(Z)-2-dibenzylamino-1-p-methoxyphenyl-3,3,3-trifluoropropene
  参考文献：
  名称：

  Concise stereoselective synthesis of 1-perfluoroalkyl enamines via the addition of N-lithiated amines to enol ethers and their subsequent metalation to form new functionalized enamines

  摘要：

  将来自多种环状、体积庞大和手性胺的锂胺与三氟甲基(Z)-烯醇醚1和4反应，可选择性地生成相应的(Z)-烯胺3a–e和7，产率良好。该反应已扩展至全氟烷基和氯氟烷基烯醇醚（CF2Cl, C2F5）。烯胺可以与ButLi反应生成烯丙负离子，随后与醛和氯乙酸乙酯反应，提供新的功能化烯胺12–16。

  DOI：

  10.1039/a801243a
• 作为产物：
  描述：

  三氟乙酸乙酯 、 p-methoxybenzyltriphenylphosphonium salt 生成 β-(trifluoromethyl)-β-ethoxy-4-methoxystrene
  参考文献：
  名称：

  The Wittig reaction of perfluoro acid derivatives: access to fluorinated enol ethers, enamines, and ketones

  摘要：

  The preparation of novel perfluoroalkyl-substituted compounds in good yields is described. This preparation involves the Wittig reaction of a phosphonium ylide with perfluoroalkyl acid derivatives. The influence of the structure of the starting alkylidenetriphenylphosphoranes, the perfluoroalkyl reagents, and the reaction conditions has been investigated. Trifluoroacetamides lead to a Z/E mixture of enamines 3. Perfluoroalkyl esters (Rf = CF3, C2F5, C3F7, C7F15, CF2Cl) lead to only the (Z)-enol ethers 8-12 when reactions are performed with NaNH2 as a base and to 1-perfluoroalkyl ketones 13-17 when reactions are performed with BuLi.

  DOI：

  10.1021/jo00040a017

文献信息

• Synthesis of Hindered and Functionalized 1-CF₃ Substituted Olefins via a Carbolithiation−Elimination−Metalation Cascade
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Denis Bouvet、Michael H. Rock

  DOI：10.1021/jo961356p

  日期：1996.1.1

  Addition of organolithium reagents to trifluoromethyl enol ethers 1a-d and thio enol ethers 2a provided stereoselectively the corresponding trisubstituted fluoroalkenes 3a-d in 70-90% yields. The products could themselves react with organolithium reagents and undergo a vinyl metalation providing, after trapping with an electrophile, tetrasubstituted olefins in excellent yields and with stereoselectivity. This method can be applied to other fluoroalkyl enol ethers (Rf = C2F5). The product, tetrasubstituted olefin, can be obtained directly from enol ether with 2 equiv of reagent through a carbolithiation-elimination-metalation cascade.