2-(tert-butyl)-4-methyl-4-(2,2,2-trifluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione | 1612841-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(tert-butyl)-4-methyl-4-(2,2,2-trifluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione
• 英文别名: 2-Tert-butyl-4-methyl-4-(2,2,2-trifluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione
• CAS: 1612841-45-8
• 化学式: C₁₆H₂₀F₃NO₂
• 分子量: 315.336
• InChiKey: OTTNTLNIPYFHBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三氟碘甲烷 、 N-(tert-butyl)-N-(4-methoxybenzyl)methacrylamide 在 fac-Ir(ppy)₃ 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以72%的产率得到2-(tert-butyl)-4-methyl-4-(2,2,2-trifluoroethyl)-2-azaspiro[4.5]deca-6,9-diene-3,8-dione
  参考文献：
  名称：

  Visible-light-induced dearomative spirocyclization of N -benzylacrylamides toward perfluorinated azaspirocyclic cyclohexadienones

  摘要：

  A feasible approach to 2-azaspirocyclic cyclohexadienones via visible-light-induced perfluoroalkylation cyclization of N-benzylacrylamides was reported. Using R-f-X (X = I or Br) as the R-f radical source, the reaction underwent a cascade radical addition/dearomative cyclization process by Ir photocatalyst, leading to various 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing perfluorinated groups including CF3, n-C3F7, n-C4F9, n-C6F13, n-C8F17, n-C10F21, CH2CF2 and CF2CO2Et. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.04.055

文献信息

• Photoredox-Catalyzed Intramolecular Difluoromethylation of <i>N</i>-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF₂H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones
  作者：Zuxiao Zhang、Xiao-Jun Tang、William R. Dolbier

  DOI：10.1021/acs.orglett.6b00168

  日期：2016.3.4

  A visible light-mediated difluoromethylation of N-benzylacrylamides with HCF2SO2Cl as the HCF2 radical precursor is described. The reaction incorporates a tandem cyclization/dearomatization process to afford various difluoromethylated 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.
• Copper-Catalyzed Intramolecular Trifluoromethylation of <i>N</i>-Benzylacrylamides Coupled with Dearomatization: Access to CF₃-Containing 2-Azaspiro[4.5]decanes
  作者：Guifang Han、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/ol501054c

  日期：2014.6.20

  Copper-catalyzed intramolecular trifluoromethylation of N-benzylacrylamides coupled with dearomatization was achieved and used to regiospecifically construct a variety of trifluoromethylated 2-azaspiro[4.5]decanes bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.