8-(4-methylphenyl)-5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 8-(4-methylphenyl)-5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazine
• 英文别名: (1R,10R)-10-(4-methylphenyl)-6,9-diazatricyclo[7.4.0.02,6]trideca-2,4-diene
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: MTUFXXBAQJBJMG-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  8.17
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(1H-吡咯-1-基)-1-乙胺 、 戊二醛 、 对甲苯基溴化镁 在 T406石油添加剂 作用下， 以 甲醇 、 水 、 四氢呋喃 为溶剂， 反应 12.0h， 以66%的产率得到8-(4-methylphenyl)-5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazine
  参考文献：
  名称：

  Novel Routes to 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines and 5,6,9,10,11,11a-Hexahydro-8H-pyrido[1,2-a]pyrrolo[2,1-c]pyrazines

  摘要：

  Condensation reactions of benzotriazole and 2-(pyrrol-1-yl)-1-ethylamine (1) with formaldehyde and glutaric dialdehyde, respectively, afforded intermediates 2 and 6. Subsequent nucleophilic substitutions of the benzotriazole group in 2 and 6 with Grignard reagents, sodium cyanide, and sodium borohydride gave 1,2,3,4-tetrahydropyrrolo[1,2-alpha]pyrazines 3a-e, 4, 5 and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-alpha]pyrrolo[2,1-c]pyrazines 7a-c, 8, 9, respectively, in good yields.

  DOI：

  10.1021/jo020371t

文献信息

• Novel Routes to 1,2,3,4-Tetrahydropyrrolo[1,2-<i>a</i>]pyrazines and 5,6,9,10,11,11a-Hexahydro-8<i>H</i>-pyrido[1,2-<i>a</i>]pyrrolo[2,1-<i>c</i>]pyrazines
  作者：Alan R. Katritzky、Ritu Jain、Yong-Jiang Xu、Peter J. Steel

  DOI：10.1021/jo020371t

  日期：2002.11.1

  Condensation reactions of benzotriazole and 2-(pyrrol-1-yl)-1-ethylamine (1) with formaldehyde and glutaric dialdehyde, respectively, afforded intermediates 2 and 6. Subsequent nucleophilic substitutions of the benzotriazole group in 2 and 6 with Grignard reagents, sodium cyanide, and sodium borohydride gave 1,2,3,4-tetrahydropyrrolo[1,2-alpha]pyrazines 3a-e, 4, 5 and 5,6,9,10,11,11a-hexahydro-8H-pyrido[1,2-alpha]pyrrolo[2,1-c]pyrazines 7a-c, 8, 9, respectively, in good yields.