N-Methyl-N-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-benzamide | 1026015-29-1

• 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: N-Methyl-N-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-benzamide
• 英文别名: N-methyl-N-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]benzamide
• CAS: 1026015-29-1
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: NQBOFJCINQAAGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(2-溴乙基)-2,5,5-三甲基-1,3-二噁烷 在 氢氧化钾 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 苯 为溶剂， 反应 5.25h， 生成 N-Methyl-N-[2-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-ethyl]-benzamide
  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.