ethyl (Z)-9-azido-10-(1,3-dioxolan-2-yl)-6-methyl-4-decenoate | 219779-46-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (Z)-9-azido-10-(1,3-dioxolan-2-yl)-6-methyl-4-decenoate
• 英文别名: ethyl (Z)-9-azido-10-(1,3-dioxolan-2-yl)-6-methyldec-4-enoate
• CAS: 219779-46-1
• 化学式: C₁₆H₂₇N₃O₄
• 分子量: 325.408
• InChiKey: IFSYDDWJCCZDLE-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-9-azido-10-(1,3-dioxolan-2-yl)-6-methyl-4-decenoate 在 四氯化碳 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙醇 、 氘代苯 、 乙腈 为溶剂， 反应 36.0h， 生成 (1S*,4R*,10R*)-4-<(1,3-dioxolan-2-yl)methyl>-1-methylquinolizidine
  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
• 作为产物：
  描述：

  [3-(乙氧羰基)丙基]三苯基溴化膦 在 叠氮化四丁基铵 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 ethyl (Z)-9-azido-10-(1,3-dioxolan-2-yl)-6-methyl-4-decenoate
  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

• 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.