Ethyl 8-methoxy-5,5-dimethyl-2-phenylchromeno[4,3-b]pyridine-3-carboxylate | 1013658-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Ethyl 8-methoxy-5,5-dimethyl-2-phenylchromeno[4,3-b]pyridine-3-carboxylate
• CAS: 1013658-65-5
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: XYYLMBIFDHKKIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-3-氨基-3-苯基-2-丙烯酸乙酯 、 3-methylene-7-methoxy-2,2-dimethylchroman-4-one 反应 5.0h， 以65%的产率得到Ethyl 8-methoxy-5,5-dimethyl-2-phenylchromeno[4,3-b]pyridine-3-carboxylate
  参考文献：
  名称：

  Diversity-Oriented Synthesis of Privileged Benzopyranyl Heterocycles from s-cis-Enones

  摘要：

  [Graphics]A novel strategy for the construction of benzopyranyl heterocyclic series with maximized diversity in the polar surface area on rigid scaffolds has been developed through a divergent synthetic pathway with high efficiency. s-cis-Enones embedded in a benzopyran skeleton were identified as versatile key intermediates for the synthesis of four different heterocycle libraries fused with a benzopyran substructure. These four novel core skeletons were designed by a creative recombination of the privileged skeletons: benzopyran, pyridine, pyrazole, pyrazolopyrimidine, and pyrimidine. The regioselective synthesis of each core skeleton was achieved by the introduction of three s-cis enone intermediates. This paper also explores the regioselective formation of arylpyrazole through the condensation of beta-keto aldehyde with arylhydrazine under three different conditions and presents the mechanistic information that was obtained from the regioisomeric ratio of arylpyrazole based on the substituent's electronic effect and reaction temperature. It appears that the regioselective synthesis of arylpyrazole was achieved through the intriguing interplay of the nucleophilicity on arylhydrazine and the electrophilicity on dielectrophiles.

  DOI：

  10.1021/jo702196f

文献信息

• Diversity-Oriented Synthesis of Privileged Benzopyranyl Heterocycles from <i>s</i>-<i>cis</i>-Enones
  作者：Heeseon An、Sung-Jin Eum、Minseob Koh、Sung Kwang Lee、Seung Bum Park

  DOI：10.1021/jo702196f

  日期：2008.3.1

  [Graphics]A novel strategy for the construction of benzopyranyl heterocyclic series with maximized diversity in the polar surface area on rigid scaffolds has been developed through a divergent synthetic pathway with high efficiency. s-cis-Enones embedded in a benzopyran skeleton were identified as versatile key intermediates for the synthesis of four different heterocycle libraries fused with a benzopyran substructure. These four novel core skeletons were designed by a creative recombination of the privileged skeletons: benzopyran, pyridine, pyrazole, pyrazolopyrimidine, and pyrimidine. The regioselective synthesis of each core skeleton was achieved by the introduction of three s-cis enone intermediates. This paper also explores the regioselective formation of arylpyrazole through the condensation of beta-keto aldehyde with arylhydrazine under three different conditions and presents the mechanistic information that was obtained from the regioisomeric ratio of arylpyrazole based on the substituent's electronic effect and reaction temperature. It appears that the regioselective synthesis of arylpyrazole was achieved through the intriguing interplay of the nucleophilicity on arylhydrazine and the electrophilicity on dielectrophiles.