2-Methyl-5-oxo-4-[1-quinolin-8-yl-meth-(Z)-ylidene]-cyclopent-1-ene-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester | 139243-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-Methyl-5-oxo-4-[1-quinolin-8-yl-meth-(Z)-ylidene]-cyclopent-1-ene-1,3-dicarboxylic acid 1-ethyl ester 3-methyl ester
• 英文别名: 1-O-ethyl 3-O-methyl 2-methyl-5-oxo-4-(quinolin-8-ylmethylidene)cyclopentene-1,3-dicarboxylate
• CAS: 139243-75-7
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: ZTPYJOXNVLBGPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-丁炔酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 polyvinylpyridine 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以9%的产率得到4H-4a,5-dicarbomethoxy-6-carbethoxy-7-methylindolo-<2,7,1-cde>quinolizine
  参考文献：
  名称：

  Reactivity of cyclopalladated compounds. 28. Alkyne reactions with the cyclopalladated 8-methylquinoline ligand. Synthesis of novel heterocyclic compounds with a bridgehead nitrogen

  摘要：

  The stepwise reaction of cyclopalladated 8-methylquinoline (compound 1, obtained via intramolecular metalation of 8-methylquinoline by Pd(II)) with 2 equiv of various internal alkynes affords 4H-indolo[2,1,7-cde]quinolizines 3 through simultaneous Pd-mediated C-C and C-N bond formation. This reaction displays a high selectivity provided that the first alkyne reacting with 1 bears two electron-withdrawing substituents such as -CF3 or -CO2Me and that the second alkyne is also substituted by electrophilic substituents. Varying the reaction conditions allowed us to isolate organometallic intermediates, whose nature shed some light upon the mechanism of the formation of 3. Several deviations from the synthesis of 3 were encountered when different alkynes were reacted with 1, e.g., with ethyl-3-phenylpropynoate a four-substituted alpha-pyrone was synthesized through C-O activation of one of the ester functions.

  DOI：

  10.1021/jo00033a042

文献信息

• Reactivity of cyclopalladated compounds. 28. Alkyne reactions with the cyclopalladated 8-methylquinoline ligand. Synthesis of novel heterocyclic compounds with a bridgehead nitrogen
  作者：Michel Pfeffer、Marc A. Rotteveel、Guy Le Borgne、Jean Fischer

  DOI：10.1021/jo00033a042

  日期：1992.3

  The stepwise reaction of cyclopalladated 8-methylquinoline (compound 1, obtained via intramolecular metalation of 8-methylquinoline by Pd(II)) with 2 equiv of various internal alkynes affords 4H-indolo[2,1,7-cde]quinolizines 3 through simultaneous Pd-mediated C-C and C-N bond formation. This reaction displays a high selectivity provided that the first alkyne reacting with 1 bears two electron-withdrawing substituents such as -CF3 or -CO2Me and that the second alkyne is also substituted by electrophilic substituents. Varying the reaction conditions allowed us to isolate organometallic intermediates, whose nature shed some light upon the mechanism of the formation of 3. Several deviations from the synthesis of 3 were encountered when different alkynes were reacted with 1, e.g., with ethyl-3-phenylpropynoate a four-substituted alpha-pyrone was synthesized through C-O activation of one of the ester functions.