N,N-diallylcoumarin-3-carboxamide | 574007-32-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N,N-diallylcoumarin-3-carboxamide
• 英文别名: 2-oxo-N,N-di(prop-2-en-1-yl)-2H-chromene-3-carboxamide；2-oxo-N,N-bis(prop-2-enyl)chromene-3-carboxamide
• CAS: 574007-32-2
• 化学式: C₁₆H₁₅NO₃
• mdl: MFCD01348458
• 分子量: 269.3
• InChiKey: JFXZJTHDRCPQRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diallylcoumarin-3-carboxamide 反应 2.0h， 以100%的产率得到
  参考文献：
  名称：

  X-ray crystallographic analysis of N,N-diallylcoumarincarboxamides and the solid-state photochemical reaction

  摘要：

  X-ray crystallographic analysis and the photochemical aspects of N,N-diallylcoumarincarboxamides were investigated. Irradiation of the corresponding amides promoted stereoselective intramolecular cyclobutane formation exclusively. The solid-state photoreaction of the coumarinamide without substituent on the 4-position proceeded in a crystal-to-crystal manner. On the other hand, photolysis of the amide possessing a methyl group at the 4-position also effected 2+2 cycloaddition; however, the reaction proceeded much slower. The difference in the reactivity was explainable on the basis of the molecular conformation in the crystal lattice. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.037
• 作为产物：
  描述：

  香豆素-3-甲酰氯 、 二烯丙基胺 以 甲苯 为溶剂， 反应 1.0h， 生成 N,N-diallylcoumarin-3-carboxamide
  参考文献：
  名称：

  X-ray crystallographic analysis of N,N-diallylcoumarincarboxamides and the solid-state photochemical reaction

  摘要：

  X-ray crystallographic analysis and the photochemical aspects of N,N-diallylcoumarincarboxamides were investigated. Irradiation of the corresponding amides promoted stereoselective intramolecular cyclobutane formation exclusively. The solid-state photoreaction of the coumarinamide without substituent on the 4-position proceeded in a crystal-to-crystal manner. On the other hand, photolysis of the amide possessing a methyl group at the 4-position also effected 2+2 cycloaddition; however, the reaction proceeded much slower. The difference in the reactivity was explainable on the basis of the molecular conformation in the crystal lattice. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.037