[1,1-bis(trifluoromethyl)buta-2,3-dien-1-yl]methyl(prop-2-yn-1-yl)amine | 1400553-84-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [1,1-bis(trifluoromethyl)buta-2,3-dien-1-yl]methyl(prop-2-yn-1-yl)amine
• CAS: 1400553-84-5
• 化学式: C₁₀H₉F₆N
• 分子量: 257.179
• InChiKey: NMRKTEWWHBZMDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [1,1-bis(trifluoromethyl)buta-2,3-dien-1-yl]methyl(prop-2-yn-1-yl)amine 、 甲氧基苯甲酰氯 在 copper(l) iodide 、 二氯双(三邻甲苯膦)合钯(II) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到4-[[1,1-bis(trifluoromethyl)buta-2,3-dien-1-yl](methyl)amino]-1-(2-methoxyphenyl)but-2-yn-1-one
  参考文献：
  名称：

  Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines

  摘要：

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.

  DOI：

  10.1021/jo301501r
• 作为产物：
  描述：

  N,N-dipropargyl-N-methylamine 、 1,1,1,3,3,3-hexafluoromethyl-2-diazopropane 在 copper(II) hexafluoroacetylacetonate 作用下， 以 苯 为溶剂， 反应 1.0h， 以50%的产率得到[1,1-bis(trifluoromethyl)buta-2,3-dien-1-yl]methyl(prop-2-yn-1-yl)amine
  参考文献：
  名称：

  Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines

  摘要：

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.

  DOI：

  10.1021/jo301501r

文献信息

• Ruthenium-catalyzed dimerization of CF3-containing functional allenes
  作者：Daria V. Vorobyeva、Anna N. Philippova、Pavel S. Gribanov、Sergey E. Nefedov、Valentine V. Novikov、Sergey N. Osipov

  DOI：10.1016/j.jorganchem.2021.121998

  日期：2021.10

  An efficient method for the regioselective preparation of 1,3-dimethylenecyclobutanes based on Ru-catalyzed dimerization of readily available CF3-containing functionalized allenes including α-amino acid derivatives have been developed. The reactions smoothly proceed in toluene at 100 °C in the presence of catalytic amounts (5 mol%) of naphthalene-containing ruthenium system [Cp*Ru(C10H8)]PF6/[Et3NBn]Cl

  已经开发了一种有效的区域选择性制备 1,3-二亚甲基环丁烷的方法，该方法基于容易获得的含CF 3的功能化丙二烯（包括 α-氨基酸衍生物）的Ru 催化二聚化。在催化量 (5 mol%) 的含萘钌体系 [Cp*Ru(C 10 H 8 )]PF 6 /[Et 3 NBn]Cl的存在下，反应在 100 °C 的甲苯中平稳进行，以独家提供尾对尾偶联产品具有良好到优异的产率。
• Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF₃-Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines
  作者：Artur K. Mailyan、Alexander S. Peregudov、Pierre H. Dixneuf、Christian Bruneau、Sergey N. Osipov

  DOI：10.1021/jo301501r

  日期：2012.10.5

  An efficient method for the synthesis of novel CF3-substituted tetrahydro-1,7-naphthyridines including cyclic alpha-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.