4-(-N-Benzoyl-N-methylamino)butan-2-one | 144587-48-4

• 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: 4-(-N-Benzoyl-N-methylamino)butan-2-one
• 英文别名: N-methyl-N-(3-oxobutyl)benzamide
• CAS: 144587-48-4
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: NIDBQILMJOCQRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(-N-Benzoyl-N-methylamino)butan-2-one 在 tetrakis(tetrabutylammonium)decatungstate(VI) 、 二甲基乙二醛肟 、 cobalt(II) benzoate 作用下， 以 乙腈 为溶剂， 以71 %的产率得到(E)-N-methyl-N-(3-oxobut-1-en-1-yl)benzamide
  参考文献：
  名称：

  光氧化还原无受体脱氢合成线性烯酰胺和烯氨基甲酸酯

  摘要：

  近年来，在光氧化还原和过渡金属催化的独特组合的推动下，开发了几种直接使脂肪族化合物去饱和的方法。因此，可以以简单的方式制备具有高功能化潜力的烯烃。我们采用了先前报道的系统，该系统涉及四丁基十钨酸铵 (TBADT) 作为氢原子转移 (HAT) 剂和用于从饱和前体脱氢制备线性烯酰胺和烯氨基甲酸酯的双氢析出的钴肟助催化剂。底物范围包括几种天然产物和药物衍生物。该反应不需要贵金属催化剂，与以往方法相比反应时间短，适用于药物衍生物的后期功能化。

  DOI：

  10.1002/adsc.202201259
• 作为产物：
  描述：

  N-Methyl-N-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-benzamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以0.13 g的产率得到4-(-N-Benzoyl-N-methylamino)butan-2-one
  参考文献：
  名称：

  Characterization of an unexpected product from a monoamine oxidase B generated 2,3-dihydropyridinium species

  摘要：

  This report summarizes the unexpected properties of the 2,3-dihydropyridinium species generated by the monoamine oxidase B catalyzed oxidation of 4-(benzoyloxy)-l-methyl-1,2,3,6-tetrahydropyridine, an analog of the neurotoxic 4-phenyltetrahydropyridine derivative. Unlike the corresponding 4-aryloxy and 4-carbamoyloxy derivatives which undergo rapid hydrolytic cleavage via a 1,4-addition of water, the benzoyloxy metabolite undergoes a 1,2-addition reaction to yield a carbinolamine that subsequently rearranges to a beta-keto aldehyde that was characterized as the corresponding pyrazole. From these results it appears that, under physiological conditions, 2,3-dihydropyridinium species in general may exist in equilibrium with the corresponding carbinolamines and ring-opened amino aldehydes, species which may be of importance in understanding the chemical and biological properties of these heterocyclic systems.

  DOI：

  10.1021/jo00052a056

文献信息

• Characterization of an unexpected product from a monoamine oxidase B generated 2,3-dihydropyridinium species
  作者：Deepak Dalvie、Zhiyang Zhao、Neal Castagnoli

  DOI：10.1021/jo00052a056

  日期：1992.12

  This report summarizes the unexpected properties of the 2,3-dihydropyridinium species generated by the monoamine oxidase B catalyzed oxidation of 4-(benzoyloxy)-l-methyl-1,2,3,6-tetrahydropyridine, an analog of the neurotoxic 4-phenyltetrahydropyridine derivative. Unlike the corresponding 4-aryloxy and 4-carbamoyloxy derivatives which undergo rapid hydrolytic cleavage via a 1,4-addition of water, the benzoyloxy metabolite undergoes a 1,2-addition reaction to yield a carbinolamine that subsequently rearranges to a beta-keto aldehyde that was characterized as the corresponding pyrazole. From these results it appears that, under physiological conditions, 2,3-dihydropyridinium species in general may exist in equilibrium with the corresponding carbinolamines and ring-opened amino aldehydes, species which may be of importance in understanding the chemical and biological properties of these heterocyclic systems.
• Synthesis of Linear Enamides and Enecarbamates <i>via</i> Photoredox Acceptorless Dehydrogenation
  作者：Ritu、Daniel Kolb、Nidhi Jain、Burkhard König

  DOI：10.1002/adsc.202201259

  日期：2023.2.21

  decatungstate (TBADT) as hydrogen atom transfer (HAT) agent and a cobaloxime co-catalyst for dihydrogen evolution for the dehydrogenative preparation of linear enamides and enecarbamates from saturated precursors. The substrate scope includes several natural products and drug derivatives. The reaction does not require noble metal catalysts, exhibits short reaction times compared to previous methods and is suitable

  近年来，在光氧化还原和过渡金属催化的独特组合的推动下，开发了几种直接使脂肪族化合物去饱和的方法。因此，可以以简单的方式制备具有高功能化潜力的烯烃。我们采用了先前报道的系统，该系统涉及四丁基十钨酸铵 (TBADT) 作为氢原子转移 (HAT) 剂和用于从饱和前体脱氢制备线性烯酰胺和烯氨基甲酸酯的双氢析出的钴肟助催化剂。底物范围包括几种天然产物和药物衍生物。该反应不需要贵金属催化剂，与以往方法相比反应时间短，适用于药物衍生物的后期功能化。