(Z)-1-diisopropylamino-2-phenyl-1-trifluoromethylethylene

• 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: (Z)-1-diisopropylamino-2-phenyl-1-trifluoromethylethylene
• 英文别名: (Z)-3,3,3-trifluoro-N,N-diisopropyl-1-phenylprop-1-en-2-amine；(Z)-3,3,3-trifluoro-1-phenyl-N,N-di(propan-2-yl)prop-1-en-2-amine
• 化学式: C₁₅H₂₀F₃N
• 分子量: 271.326
• InChiKey: OACAZWLIWVVCRG-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-氯-3,3,3-三氟丙-1-烯基)苯 、 二异丙胺 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到(Z)-1-diisopropylamino-2-phenyl-1-trifluoromethylethylene
  参考文献：
  名称：

  Regio- and stereoselective synthesis of chiral (αS)-(Z)-trifluoromethyl-β-aryl-enamines

  摘要：

  Chiral (alphaS)-(Z)-trifluoromethyl-beta-aryl-enamines were regio and stereoselectiveally prepared in excellent yields by the one pot reaction of 2-aryl-1-chloro-1-trifluoromethylethlene with lithium (alphaS)-(alpha-methylbenzyl) benzylamide. A mechanism involving elimination and addition processes is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01156-5

文献信息

• 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
  作者：Jean-Pierre Bégué、Danièle Bonnet-Delpon、Denis Bouvet、Michael H. Rock

  DOI：10.1039/a801243a

  日期：——

  Addition of lithium amides derived from a range of cyclic, sterically demanding, and chiral amines, to trifluoromethyl (Z)-enol ethers 1 and 4, provides stereoselectively the corresponding (Z)-enamines 3a–e and 7 in good yields. This reaction has been extended to the perfluoroalkyl and chlorofluoroalkyl enol ethers (CF2Cl, C2F5). The enamines can react with ButLi to give vinylic anions and, after quenching with aldehydes and ethyl chloroformate, provide new functionalized enamines 12–16.

  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。
• Palladium-catalyzed amination of 2,3,3-trifluoroallyl esters: synthesis of trifluoromethylenamines via an intramolecular fluorine shift and CF₃ group construction
  作者：Kazuki Isa、Maki Minakawa、Motoi Kawatsura

  DOI：10.1039/c5cc01212k

  日期：——

  The palladium-catalyzed reaction of 2,3,3-trifluoroallyl esters with amines afforded trifluoromethylenamines, which were formed by the addition of a nitrogen nucleophile at the C-2 position and the fluorine atom shift from the C-2 to C-3 position.

  2,3,3-三氟丙烯酸酯与胺的钯催化反应产生了三氟甲亚胺，这是通过氮亲核试剂在C-2位置加成以及氟原子从C-2位置转移到C-3位置而形成的。