N-(tert-butyl)-N-(4-hydroxybenzyl)methacrylamide | 1612841-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(tert-butyl)-N-(4-hydroxybenzyl)methacrylamide
• CAS: 1612841-30-1
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: NCMCRXOGAOTUMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)-N-(4-hydroxybenzyl)methacrylamide 在 ammonium cerium (IV) nitrate 、 5%-palladium/activated carbon 、 水 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(tert-butyl)-4-methyl-4-(((trifluoromethyl)thio)methyl)-2-azaspiro[4.5]decane-3,8-dione
  参考文献：
  名称：

  CAN-Promoted Thiolative ipso-Annulation of Unactivated N-Benzyl Acrylamides: Access to SCN/SCF₃/SO₂Ar Containing Azaspirocycles

  摘要：

  DOI：

  10.1021/acs.joc.3c00374

文献信息

• Palladium-catalyzed difunctionalization/dearomatization of <i>N</i>-benzylacrylamides with α-carbonyl alkyl bromides: facile access to azaspirocyclohexadienones
  作者：Chuan-Chong Peng、Li-Jun Wu、Shao-Feng Pi

  DOI：10.1039/d1ob01405f

  日期：——

  An efficient palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides as alkyl radical precursors has been described. Various α-carbonyl alkyl bromides, including α-bromoalkyl esters and ketones, reacted smoothly to provide important azaspirocyclohexadienones in moderate to excellent yields. In addition, mechanistic studies suggested that the reaction

  已经描述了以 α-羰基烷基溴化物作为烷基自由基前体的N-苄基丙烯酰胺的有效钯催化双官能化/脱芳构化。各种 α-羰基烷基溴化物，包括 α-溴烷基酯和酮，反应平稳，以中等至优异的产率提供重要的氮杂螺环己二烯酮。此外，机理研究表明反应通过自由基途径进行。
• Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives <i>via</i> copper-catalyzed difluoroalkylation/dearomatization of <i>N</i>-benzylacrylamides
  作者：Chengwen Li、Yilin Zhao、Jiaxin Zhou、Xue Wang、Jingli Hou、Yuguang Song、Wenjuan Liu、Guifang Han

  DOI：10.1039/d0ob01833c

  日期：——

  An efficient method for the synthesis of difluoroalkylated 2-azaspiro[4.5]decanes via copper-catalyzed difluoroalkylation of N-benzylacrylamides with ethyl bromodifluoroacetate has been established. The reaction experienced a tandem radical addition and dearomatizing cyclization process. In addition, the resultant products can be smoothly converted into a difluoroalkylated quinolinone and saturated

  建立了一种铜催化N-苄基丙烯酰胺与溴二氟乙酸乙酯进行二氟烷基化合成二氟烷基化2-氮杂螺[4.5]癸烷的有效方法。该反应经历了串联自由基加成和脱芳构化环化过程。此外，所得产物可以顺利转化为二氟烷基化喹啉酮和饱和螺环己酮支架。
• 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.
• Electrochemical selenylative ipso-annulation of N-benzylacrylamides to construct seleno-azaspiro[4.5]decadienones
  作者：Chada Raji Reddy、Jannatul Islam、Thallamapuram Nagendraprasad、Uprety Ajaykumar

  DOI：10.1039/d4ob00805g

  日期：——

  Construction of seleno azaspiro[4.5]decadienones using an electrochemical approach is achieved via domino selenylation/ipso-annulation.