1-(2,4-dimethoxybenzyl)-1,3,4,5-tetrahydro-1H-azepin-2-one | 1009808-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2,4-dimethoxybenzyl)-1,3,4,5-tetrahydro-1H-azepin-2-one
• CAS: 1009808-86-9
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: LCAXQWOKCZMPRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  重氮乙酸乙酯 、 1-(2,4-dimethoxybenzyl)-1,3,4,5-tetrahydro-1H-azepin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 、 ethyl (1SR,7SR,8SR)-2-(2,4-dimethoxybenzyl)-3-oxo-2-azabicyclo[5.1.0]octane-8-carboxylate 、 ethyl (1SR,7SR,8RS)-2-(2,4-dimethoxybenzyl)-3-oxo-2-azabicyclo[5.1.0]octane-8-carboxylate
  参考文献：
  名称：

  Tandem RCM−Isomerization− Cyclopropanation Reactions

  摘要：

  A new triple tandem process has been discovered in which simple acyclic substrates can be transformed into bicyclic compounds via RCM-double bond isomerization-cyclopropanation. This process is catalyzed by second generation Grubb's catalyst without the requirement of other reactives or additives. In addition, a one-pot RCM-isomerization reaction followed by cyclopropanation with CHCl3/NaOH allows the synthesis of products related to NOS (nitric oxide synthase) inhibitors, which are currently under clinical evaluation.

  DOI：

  10.1021/ol702766h
• 作为产物：
  描述：

  N-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylpent-4-enamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以62%的产率得到1-(2,4-dimethoxybenzyl)-1,3,4,5-tetrahydro-1H-azepin-2-one
  参考文献：
  名称：

  Tandem RCM−Isomerization− Cyclopropanation Reactions

  摘要：

  A new triple tandem process has been discovered in which simple acyclic substrates can be transformed into bicyclic compounds via RCM-double bond isomerization-cyclopropanation. This process is catalyzed by second generation Grubb's catalyst without the requirement of other reactives or additives. In addition, a one-pot RCM-isomerization reaction followed by cyclopropanation with CHCl3/NaOH allows the synthesis of products related to NOS (nitric oxide synthase) inhibitors, which are currently under clinical evaluation.

  DOI：

  10.1021/ol702766h