(1R,2S,9S)-11-(n-butyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane | 71635-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (1R,2S,9S)-11-(n-butyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane
• 英文别名: (1R)-3-butyl-(11ac)-decahydro-1r,5c-methano-pyrido[1,2-a][1,5]diazocine；(1R)-3-Butyl-(11ac)-decahydro-1r,5c-methano-pyrido[1,2-a][1,5]diazocin；(1R,2S,9S)-11-butyl-7,11-diazatricyclo[7.3.1.02,7]tridecane
• CAS: 71635-25-1
• 化学式: C₁₅H₂₈N₂
• 分子量: 236.401
• InChiKey: VQAVPDFOXQFIHH-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cytisine 在 盐酸 、 铂 作用下， 生成 (1R,2S,9S)-11-(n-butyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane
  参考文献：
  名称：

  THE PAPILIONACEOUS ALKALOIDS: XV. THE STRUCTURE AND THE PARTIAL SYNTHESIS OF RHOMBIFOLINE

  摘要：

  Rhombifoline与thermopsine和anagyrine同分异构体，像这两种生物碱一样，含有α-吡啶酮环。它可以被去烷基化为细胞嘧啶，经催化氢化反应后产生八氢脱氧罗姆比福林，这与六氢脱氧-N-(正丁基)-细胞嘧啶相同，后者是N-(正丁基)-细胞嘧啶的氢化产物。因此，氢化的结果表明，罗姆比福林分子含有第三个双键，其红外光谱显示它位于一个末端亚甲基基团。因此，罗姆比福林是N-(丁-3-烯基)-细胞嘧啶，这一结论通过从细胞嘧啶部分合成生物碱得到确认。

  DOI：

  10.1139/v52-014

文献信息

• Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis
  作者：Michael J. Dearden、Matthew J. McGrath、Peter O'Brien

  DOI：10.1021/jo049182w

  日期：2004.8.1

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.
• THE PAPILIONACEOUS ALKALOIDS: XV. THE STRUCTURE AND THE PARTIAL SYNTHESIS OF RHOMBIFOLINE
  作者：William F. Cockburn、Léo Marion

  DOI：10.1139/v52-014

  日期：1952.2.1

  Rhombifoline is isomeric with thermopsine and anagyrine, and, like both these alkaloids, contains an α-pyridone ring. It can be dealkylated to cytisine, and, on catalytic hydrogenation, yields octahydrodesoxyrhombifoline, which is identical with hexahydrodesoxy-N-(n-butyl)-cytisine, the hydrogenation product of N-(n-butyl)-cytisine. The results of the hydrogenation thus indicate that the molecule of rhombifoline contains a third double bond, which is shown by its infrared spectrum to be located at a terminal methylene group. Rhombifoline is therefore N-(but-3-enyl)-cytisine, a conclusion which was confirmed by the partial synthesis of the alkaloid from cytisine.

  Rhombifoline与thermopsine和anagyrine同分异构体，像这两种生物碱一样，含有α-吡啶酮环。它可以被去烷基化为细胞嘧啶，经催化氢化反应后产生八氢脱氧罗姆比福林，这与六氢脱氧-N-(正丁基)-细胞嘧啶相同，后者是N-(正丁基)-细胞嘧啶的氢化产物。因此，氢化的结果表明，罗姆比福林分子含有第三个双键，其红外光谱显示它位于一个末端亚甲基基团。因此，罗姆比福林是N-(丁-3-烯基)-细胞嘧啶，这一结论通过从细胞嘧啶部分合成生物碱得到确认。