3-cyano-4-hydroxy-2-phenylpyrido[1,2-b]pyridazinium inner salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-cyano-4-hydroxy-2-phenylpyrido[1,2-b]pyridazinium inner salt
• 英文别名: 3-cyano-2-phenylpyrido[1,2-b]pyridazin-9-ium-4-olate
• 化学式: C₁₅H₉N₃O
• 分子量: 247.256
• InChiKey: XMUFUKVSXQGHJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.84
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (肉)桂腈 、 1-amino-2-(ethoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以30%的产率得到3-cyano-4-hydroxy-2-phenylpyrido[1,2-b]pyridazinium inner salt
  参考文献：
  名称：

  2-Alkoxycarbonylpyridinium N-Aminides:  1,3-Dipoles or 1,4-Nucleophile−Electrophile Synthons? Experimental and Theoretical Evidence for the Mechanism of Pyrido[1,2-b]pyridazinium Inner Salt Formation

  摘要：

  2-Alkoxycarbonylpyridinium N-aminides behave as 1,3-dipoles toward acetylenic compounds and as 1,4-nucleophile-electrophiles with heterocumulenes in a [4 + 2] cyclocondensation process, yielding in the latter case conjugated mesomeric betaines. These N-aminides also behave as 1,3-dipoles when reacted with olefinic dipolarophiles, producing the corresponding cycloadducts that, depending on their regioisomeric nature, subsequently undergo a ring expansion process to produce pyrido[1,2-b]-pyridazinium inner salts. A mechanistic investigation performed using both PM3 frontier molecular orbital (FMO) and potential energy surface (PES) analysis at the RHF/6-31+G* level indicates that both the cycloaddition reaction and the ring expansion occur in a concerted way rather than through a stepwise mechanism via a zwitterionic intermediate.

  DOI：

  10.1021/jo9909655

文献信息

• New route to pyrido[1,2-b]pyridazinium inner salts. Evidence of a 1,3-dipolar cycloaddition-ring expansion process
  作者：Jesús Valenciano、Ana M. Cuadro、Juan J. Vaquero、Julio Alvarez-Builla

  DOI：10.1016/s0040-4039(98)02406-x

  日期：1999.1

  reacted with Michael acceptors, giving rise to the corresponding cycloadducts which, depending on their regioisomeric nature, subsequently undergo a ring expansion to give pyrido[1,2-b]pyridazinium inner salts.

  2-烷氧羰基吡啶鎓N-氨基化物与迈克尔受体反应时表现为1,3-偶极子，产生相应的环加合物，取决于其区域异构体性质，随后进行环扩环，使吡啶并[1,2- b ]吡啶鎓内部盐。
• 2-Alkoxycarbonylpyridinium N-Aminides:  1,3-Dipoles or 1,4-Nucleophile−Electrophile Synthons? Experimental and Theoretical Evidence for the Mechanism of Pyrido[1,2-<i>b</i>]pyridazinium Inner Salt Formation
  作者：Jesús Valenciano、Ana M. Cuadro、Juan J. Vaquero、Julio Alvarez-Builla、Raul Palmeiro、Obis Castaño

  DOI：10.1021/jo9909655

  日期：1999.12.1

  2-Alkoxycarbonylpyridinium N-aminides behave as 1,3-dipoles toward acetylenic compounds and as 1,4-nucleophile-electrophiles with heterocumulenes in a [4 + 2] cyclocondensation process, yielding in the latter case conjugated mesomeric betaines. These N-aminides also behave as 1,3-dipoles when reacted with olefinic dipolarophiles, producing the corresponding cycloadducts that, depending on their regioisomeric nature, subsequently undergo a ring expansion process to produce pyrido[1,2-b]-pyridazinium inner salts. A mechanistic investigation performed using both PM3 frontier molecular orbital (FMO) and potential energy surface (PES) analysis at the RHF/6-31+G* level indicates that both the cycloaddition reaction and the ring expansion occur in a concerted way rather than through a stepwise mechanism via a zwitterionic intermediate.