7-hexyl-1,8a-dimethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyriamidin-6(8aH)-one | 1418740-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-hexyl-1,8a-dimethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyriamidin-6(8aH)-one
• 英文别名: 7-hexyl-1,8a-dimethyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrimidin-6-one
• CAS: 1418740-37-0
• 化学式: C₁₅H₂₆N₂O
• 分子量: 250.384
• InChiKey: NYPUMUXCZKQJLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-辛炔 、 一氧化碳 、 1,2-二甲基-1,4,5,6-四氢嘧啶 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64%的产率得到7-hexyl-1,8a-dimethyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyriamidin-6(8aH)-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.