N-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylprop-2-enamide | 1009808-78-9

• 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-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylprop-2-enamide
• 英文别名: N-[(2,4-dimethoxyphenyl)methyl]-N-prop-2-enylprop-2-enamide
• CAS: 1009808-78-9
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: ZHUSLSRKUIPPHI-UHFFFAOYSA-N

物化性质

• 沸点：
  427.1±45.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylprop-2-enamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到1-(2,4-二甲氧基苄基)-1,5-二氢-2H-吡咯-2-酮
  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)-prop-2-en-1-amine 、 3-氯丙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到N-(2,4-dimethoxybenzyl)-N-prop-2-en-1-ylprop-2-enamide
  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

文献信息

• Cycloisomerization of dienes and enynes catalysed by a modified ruthenium carbene species
  作者：Álvaro Mallagaray、Kazem Mohammadiannejad-Abbasabadi、Sandra Medina、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1039/c2ob07185a

  日期：——

  Cycloisomerization is a totally atom economic procedure which converts dienes and enynes into cyclic molecules. Modification of Grubbs’ 2nd generation catalysts by reaction with dimethylformamide provides a new species able to catalyse this transformation. Selection of suitable conditions allowed high yields and selectivity. Studies performed in order to identify the catalytic species point to a non-carbenic

  环异构化是一种完全原子经济的方法，可将二烯和烯炔转化为环状分子。通过与Grubbs的第二代催化剂反应改性二甲基甲酰胺提供了能够催化这种转化的新物种。选择合适的条件可以实现高收率和选择性。为了鉴定催化物种而进行的研究指出了失去膦的非碳烯钌络合物。没有氢化物信号出现。此外，该反应可与烯炔一起使用，新物质可有效催化炔烃与二炔的交叉三环化反应。
• Tandem RCM−Isomerization− Cyclopropanation Reactions
  作者：Álvaro Mallagaray、Gema Domínguez、Ana Gradillas、Javier Pérez-Castells

  DOI：10.1021/ol702766h

  日期：2008.2.1

  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.