1-((E)-3,3-dimethyl-2-(trifluoromethyl)-1-butenyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((E)-3,3-dimethyl-2-(trifluoromethyl)-1-butenyl)benzene
• 英文别名: E-2-trifloromethyl-2-t-butyl styrene；(E)-(3,3-Dimethyl-2-trifluoromethyl-but-1-enyl)-benzene；[(E)-3,3-dimethyl-2-(trifluoromethyl)but-1-enyl]benzene
• 化学式: C₁₃H₁₅F₃
• 分子量: 228.257
• InChiKey: JPTWBTGEFLLLEM-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙醛 、 1-((E)-3,3-dimethyl-2-(trifluoromethyl)-1-butenyl)benzene 在 四甲基乙二胺 、 叔丁基锂 作用下， 生成 (Z)-2,2-dimethyl-5-hydroxy-4-phenyl-3-trifluoromethylhept-3-ene
  参考文献：
  名称：

  Synthesis of Hindered and Functionalized 1-CF₃ Substituted Olefins via a Carbolithiation−Elimination−Metalation Cascade

  摘要：

  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.

  DOI：

  10.1021/jo961356p
• 作为产物：
  描述：

  叔丁基锂 、 (Z)-(2-ethoxy-3,3,3-trifluoroprop-1-enyl)benzene 以 乙醚 、 正己烷 为溶剂， 以84%的产率得到1-((E)-3,3-dimethyl-2-(trifluoromethyl)-1-butenyl)benzene
  参考文献：
  名称：

  Z-三氟甲基硫代烯醇醚，烯醇醚和烯胺；对有机锂试剂的反应性

  摘要：

  与有机锂试剂进行加/消除反应的，在β位上与不饱和键合的三氟甲基烯醇醚和硫代烯醇醚，生成相应的三氟甲基烯烃，同时保留了双键的几何形状。三氟甲基烯胺对有机锂试剂表现出不同的反应性，其中乙烯基阴离子优先于加成/消除产物而形成。

  DOI：

  10.1016/0040-4039(95)02118-3

文献信息

• Z-trifluoromethyl thioenol ethers, enol ethers, and enamines; reactivity towards organolithium reagents
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Michael H. Rock

  DOI：10.1016/0040-4039(95)02118-3

  日期：1996.1

  conjugated with an unsaturation in the β-position undergo addition/elimination reactions with organolithium reagents to yield the corresponding trifluoromethyl alkenes while preserving the geometry of the double bond. Trifluoromethyl enamines exhibit a different reactivity towards organolithium reagents with a vinyl anion being formed in preference to addition/elimination products.

  与有机锂试剂进行加/消除反应的，在β位上与不饱和键合的三氟甲基烯醇醚和硫代烯醇醚，生成相应的三氟甲基烯烃，同时保留了双键的几何形状。三氟甲基烯胺对有机锂试剂表现出不同的反应性，其中乙烯基阴离子优先于加成/消除产物而形成。
• Short Stereoselective Route to γ-CF₃ Allylic Alcohols:  Rearrangements with Creation of Quaternary CF₃-Substituted Carbons
  作者：Denis Bouvet、Hamid Sdassi、Michèle Ourévitch、Danièle Bonnet-Delpon

  DOI：10.1021/jo991702d

  日期：2000.4.1

  A concise preparation of tetrasubstituted hindered functionalized CF3-olefins 2-7 from corresponding enol ether 3 is described. Geometrically pure gamma-CF3,gamma-alkyl allylic alcohol thus prepared could undergo Claisen-type rearrangements and provide, in good yields, carboxylic esters and amides containing a beta- quaternary CF3-substituted carbon.
• 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.