2-(4-methoxy)phenyl-5,6,8,9,10,11-hexahydro-4H,7H-3a,6a-diaza-cyclohepta[d]inden-3-one | 1418740-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxy)phenyl-5,6,8,9,10,11-hexahydro-4H,7H-3a,6a-diaza-cyclohepta[d]inden-3-one
• 英文别名: 3-(4-Methoxyphenyl)-5,9-diazatricyclo[7.5.0.01,5]tetradec-2-en-4-one；3-(4-methoxyphenyl)-5,9-diazatricyclo[7.5.0.01,5]tetradec-2-en-4-one
• CAS: 1418740-34-7
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: NGSVDLZRDXQHON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  一氧化碳 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-乙炔基苯甲醚 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 80.0 ℃ 、8.11 MPa 条件下， 反应 6.0h， 以58%的产率得到2-(4-methoxy)phenyl-5,6,8,9,10,11-hexahydro-4H,7H-3a,6a-diaza-cyclohepta[d]inden-3-one
  参考文献：
  名称：

  Free-Radical-Mediated [2 + 2 + 1] Cycloaddition of Acetylenes, Amidines, and CO Leading to Five-Membered α,β-Unsaturated Lactams

  摘要：

  A free-radical-mediated [2 + 2 + 1] cycloaddition reaction comprising acetylenes, amidines, and CO was achieved by radical chain reaction to give five-membered alpha,beta-unsaturated lactams in good yields. Both acyclic and cyclic amidines reacted with a variety of terminal acetylenes to afford monocyclic, bicyclic, and tricyclic lactams. We propose that vinyl radical carbonylation and nucleophilic addition of the amidine onto the resulting a-ketenyl radical give stable intermediates that are ready to undergo five-membered ring closure with elimination of tin radical.

  DOI：

  10.1021/ja312654q

文献信息

• Free-Radical-Mediated [2 + 2 + 1] Cycloaddition of Acetylenes, Amidines, and CO Leading to Five-Membered α,β-Unsaturated Lactams
  作者：Takahide Fukuyama、Nao Nakashima、Takuma Okada、Ilhyong Ryu

  DOI：10.1021/ja312654q

  日期：2013.1.23

  A free-radical-mediated [2 + 2 + 1] cycloaddition reaction comprising acetylenes, amidines, and CO was achieved by radical chain reaction to give five-membered alpha,beta-unsaturated lactams in good yields. Both acyclic and cyclic amidines reacted with a variety of terminal acetylenes to afford monocyclic, bicyclic, and tricyclic lactams. We propose that vinyl radical carbonylation and nucleophilic addition of the amidine onto the resulting a-ketenyl radical give stable intermediates that are ready to undergo five-membered ring closure with elimination of tin radical.