N-(tert-butyl)-2-methyl-3-oxo-3-phenylpropanamide | 42222-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(tert-butyl)-2-methyl-3-oxo-3-phenylpropanamide
• 英文别名: 2-Benzoyl-N-tert.-butyl-propionamid
• CAS: 42222-08-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: TXBXHXBPFJAWKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.17
• 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)-2-methyl-3-oxo-3-phenylpropanamide 在 N-(苯磺酰基)-N-甲基苯磺酰胺 、 C₁₀₄H₉₈O₂P₄Pd₂⁽²⁺⁾*2CF₃O₃S^(1-) 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以65%的产率得到
  参考文献：
  名称：

  Unique features of chiral palladium enolates derived from β-ketoamide: structure and catalytic asymmetric Michael and fluorination reactions

  摘要：

  We have previously reported enantioselective reactions of 1,3 -diketones and beta-ketoesters with various electrophiles catalyzed by chiral Pd complex, in which chiral Pd enolates play a key role. Here, we present a detailed examination of Pd-catalyzed enantioselective Michael addition and fluorination reactions of beta-ketoamides. beta-Ketoamide showed higher reactivity than 1,3-diketone and beta-ketoester, though its alpha-proton is likely to be least acidic. Pd enolate formation of beta-ketoamide was much faster than that of beta-ketoester. The crystal structures of (R)-BINAP-Pd-diketone and ketoamide complexes were found to be quite distinct. Pd-diketone complex has bidentate square-planar geometry as have been predicted before, whereas Pd-ketoamide complex was greatly distorted, probably due to steric constraints of the amide bond. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.002
• 作为产物：
  描述：

  2-tert-butyl-4-methyl-5-phenyl-isoxazolium; perchlorate 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 N-(tert-butyl)-2-methyl-3-oxo-3-phenylpropanamide
  参考文献：
  名称：

  在将羧酸添加到N-叔丁基丁烯酮亚胺中的过程中进行N-酰化，并使用试剂N-叔丁基-5-甲基异恶唑鎓高氯酸盐进行肽合成。

  摘要：

  DOI：

  10.1021/jo00964a018

文献信息

• α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity
  作者：Mathias Mamboury、Qian Wang、Jieping Zhu

  DOI：10.1002/chem.201703458

  日期：2017.9.18

  β-Hydride elimination at will: Reaction of α-haloketones with isocyanides in the presence of a catalytic amount of Pd(OAc)2 afforded α-oxo-ketenimines that can be further converted to 5-aminopyrazoles, tetrazole, β-keto amidines and enaminone in good to excellent yields.

  随意消除β-氢化物：在催化量的Pd（OAc）2存在下，α-卤代酮与异氰酸酯反应，得到α-氧代-酮亚胺，可以进一步转化为5-氨基吡唑，四唑，β-酮am和烯胺酮的收率好至极好。
• Enantioselective Radical‐Polar Crossover Reactions of Indanonecarboxamides with Alkenes
  作者：Xiying Zhang、Wangbin Wu、Weidi Cao、Han Yu、Xi Xu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/anie.201914151

  日期：2020.3.16

  Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N'-dioxide/NiII complex catalyst with Ag2 O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities

  通过在温和的反应条件下，将手性N，N'-二氧化物/ NiII复合催化剂与Ag2 O结合，可以实现高效的不对称分子间自由基-极性交叉反应。各种末端烯烃和茚满羧酰胺/酯经过自由基加成/环化反应，得到螺亚氨基内酯和螺内酯，具有良好至优异的收率（高达99％）和对映选择性（高达97％ee）。此外，在温和的反应条件下获得了一系列不同的自由基介导的氧化/消除或环氧化物开环产物。路易斯酸催化剂表现出优异的性能并且排除了强烈的背景反应。