N-(2,3,3a,4,7,7a-hexahydro-2,5-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-3-phenylpropiolamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2,3,3a,4,7,7a-hexahydro-2,5-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-3-phenylpropiolamide
• 英文别名: N-[(3aS,4S,7aS)-2,5-dimethyl-1,3-dioxo-3a,4,7,7a-tetrahydroisoindol-4-yl]-3-phenylprop-2-ynamide
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: CDOXSPNUQGCXIN-BHYGNILZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,3,3a,4,7,7a-hexahydro-2,5-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-3-phenylpropiolamide 、 碘甲烷 在 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以61%的产率得到N-(2,3,3a,4,7,7a-hexahydro-2,5-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-N-methyl-3-phenylpropiolamide
  参考文献：
  名称：

  A facile and efficient synthesis of enyne-reaction precursors by multicomponent reactions

  摘要：

  Using improved reaction protocols for three-component coupling reactions of aldehydes, dienophiles, and amides (AAD-reaction) or anhydrides (ANAD-reaction) or orthoesters (ALAD-reaction), a variety of functionalized hexahydroisoindolo derivatives were synthesized and fully characterized. Condensation of ubiquitous available aldehydes with unsaturated amides or anhydrides or orthoesters and subsequent Diels-Alder reactions with electron deficient dienophiles furnishes endo-selective enyne-reaction precursors in good to excellent yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.097
• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 反式-2-甲基-2-丁烯醛 、 3-苯基丙-2-炔酰胺 在 乙酸酐 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以81%的产率得到N-(2,3,3a,4,7,7a-hexahydro-2,5-dimethyl-1,3-dioxo-1H-isoindol-4-yl)-3-phenylpropiolamide
  参考文献：
  名称：

  A facile and efficient synthesis of enyne-reaction precursors by multicomponent reactions

  摘要：

  Using improved reaction protocols for three-component coupling reactions of aldehydes, dienophiles, and amides (AAD-reaction) or anhydrides (ANAD-reaction) or orthoesters (ALAD-reaction), a variety of functionalized hexahydroisoindolo derivatives were synthesized and fully characterized. Condensation of ubiquitous available aldehydes with unsaturated amides or anhydrides or orthoesters and subsequent Diels-Alder reactions with electron deficient dienophiles furnishes endo-selective enyne-reaction precursors in good to excellent yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.097

文献信息

• A facile and efficient synthesis of enyne-reaction precursors by multicomponent reactions
  作者：Dirk Strübing、Helfried Neumann、Stefan Klaus、Sandra Hübner、Matthias Beller

  DOI：10.1016/j.tet.2005.09.097

  日期：2005.11

  Using improved reaction protocols for three-component coupling reactions of aldehydes, dienophiles, and amides (AAD-reaction) or anhydrides (ANAD-reaction) or orthoesters (ALAD-reaction), a variety of functionalized hexahydroisoindolo derivatives were synthesized and fully characterized. Condensation of ubiquitous available aldehydes with unsaturated amides or anhydrides or orthoesters and subsequent Diels-Alder reactions with electron deficient dienophiles furnishes endo-selective enyne-reaction precursors in good to excellent yield. (c) 2005 Elsevier Ltd. All rights reserved.