1,2,3,4,6,7,8,9-octahydro-quinolizinylium chloride

• 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: 1,2,3,4,6,7,8,9-octahydro-quinolizinylium chloride
• 英文别名: 1,2,3,4,6,7,8,9-Octahydroquinolizin-5-ium;chloride
• 化学式: C₉H₁₆N*Cl
• 分子量: 173.686
• InChiKey: CAWLKPGFNCHBAC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6,7,8,9-octahydro-quinolizinylium chloride 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以70%的产率得到八氢-4H-喹嗪
  参考文献：
  名称：

  吲哚并idine啶和喹oli嗪的新型合成

  摘要：

  通过2-甲基-1-吡咯啉或6-甲基-2,3,4,5-四氢吡啶与1,3-或1,4-二卤代烷烃的烷基化反应，开发了吲哚唑烷，喹喔啉和一些更高同系物的非常短的合成方法，然后还原中间亚胺盐，得到所需的1-氮杂双环[ m]。n .0]烷烃收率高。

  DOI：

  10.1016/s0040-4020(03)00375-2
• 作为产物：
  描述：

  (Z)-9-Azido-1-chloro-non-4-ene 以 氘代氯仿 为溶剂， 反应 56.0h， 生成 1,2,3,4,6,7,8,9-octahydro-quinolizinylium chloride
  参考文献：
  名称：

  Total Synthesis of (±)-Quinolizidine 217A

  摘要：

  Several 1,4-disubstituted quinolizidines have been isolated in minute quantities from the skin of certain poisonous frogs and toads. The structures of these alkaloids have been proposed mainly on the basis of MS and IR spectroscopic data. We report the first total synthesis of a naturally occurring alkaloid of this type, quinolizidine 217A. After examination of several azide-based routes, the cyclization of an azide onto an ester-bearing alkene provided a 3,4,5,6-tetrahydropyridine that was reduced in a stereoselective fashion to produce a cis-2,6-disubstituted piperidine (25 --> 31 --> 32). Transformation of 32 into quinolizidine 217A (2) and its C(1) epimer (41) were accomplished in a straightforward fashion. Synthetic quinolizidine 217A was found to be identical to the natural alkaloid, confirming its stereostructure. Compound 41 has the same stereostructure as that proposed for the alkaloid quinolizidine 207I, a compound whose configuration was recently revised as a result of synthetic studies by Momose et al., who synthesized a 1,4-disubstituted quinolizidine with the configuration previously proposed for quinolizidine 207I and found the synthetic material to be epimeric with the natural material. Compound 41 should provide a useful point of comparison for future studies on the stereostructure of natural or synthetic quinolizidine 207I.

  DOI：

  10.1021/jo981695d

文献信息

• Novel synthesis of indolizidines and quinolizidines
  作者：Kourosch Abbaspour Tehrani、Matthias D'hooghe、Norbert De Kimpe

  DOI：10.1016/s0040-4020(03)00375-2

  日期：2003.4

  A very short synthesis of indolizidines, quinolizidines and some higher homologues was developed by alkylation of 2-methyl-1-pyrroline or 6-methyl-2,3,4,5-tetrahydropyridine with 1,3- or 1,4-dihaloalkanes, followed by reduction of the intermediate iminium salts, resulting in the desired 1-azabicyclo[m.n.0]alkanes in good yields.

  通过2-甲基-1-吡咯啉或6-甲基-2,3,4,5-四氢吡啶与1,3-或1,4-二卤代烷烃的烷基化反应，开发了吲哚唑烷，喹喔啉和一些更高同系物的非常短的合成方法，然后还原中间亚胺盐，得到所需的1-氮杂双环[ m]。n .0]烷烃收率高。
• Total Synthesis of (±)-Quinolizidine 217A
  作者：William H. Pearson、Hiroyuki Suga

  DOI：10.1021/jo981695d

  日期：1998.12.1

  Several 1,4-disubstituted quinolizidines have been isolated in minute quantities from the skin of certain poisonous frogs and toads. The structures of these alkaloids have been proposed mainly on the basis of MS and IR spectroscopic data. We report the first total synthesis of a naturally occurring alkaloid of this type, quinolizidine 217A. After examination of several azide-based routes, the cyclization of an azide onto an ester-bearing alkene provided a 3,4,5,6-tetrahydropyridine that was reduced in a stereoselective fashion to produce a cis-2,6-disubstituted piperidine (25 --> 31 --> 32). Transformation of 32 into quinolizidine 217A (2) and its C(1) epimer (41) were accomplished in a straightforward fashion. Synthetic quinolizidine 217A was found to be identical to the natural alkaloid, confirming its stereostructure. Compound 41 has the same stereostructure as that proposed for the alkaloid quinolizidine 207I, a compound whose configuration was recently revised as a result of synthetic studies by Momose et al., who synthesized a 1,4-disubstituted quinolizidine with the configuration previously proposed for quinolizidine 207I and found the synthetic material to be epimeric with the natural material. Compound 41 should provide a useful point of comparison for future studies on the stereostructure of natural or synthetic quinolizidine 207I.