5-<(Z)-2-<5-(4-chlorophenyl)-2H-tetrazol-4-yl>vinyl>-4-methyl-2,5-dihydropyridazine-3,6-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-<(Z)-2-<5-(4-chlorophenyl)-2H-tetrazol-4-yl>vinyl>-4-methyl-2,5-dihydropyridazine-3,6-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 4-[(Z)-2-[2-(4-chlorophenyl)tetrazol-5-yl]ethenyl]-5-methyl-1,4-dihydropyridazine-3,6-dicarboxylate
• 化学式: C₁₈H₁₇ClN₆O₄
• 分子量: 416.824
• InChiKey: ZYCSNAUBYCKLBI-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,2,4,5-四嗪-3,6-二羧酸二甲酯 、 以 甲苯 为溶剂， 反应 0.75h， 生成 5-<(Z)-2-<5-(4-chlorophenyl)-2H-tetrazol-4-yl>vinyl>-4-methyl-2,5-dihydropyridazine-3,6-dicarboxylic acid dimethyl ester 、 5-<(Z)-2-<5-(4-chlorophenyl)-2H-tetrazol-4-yl>vinyl>-4-methyl-1,4-dihydropyridazine-3,6-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Expected Selectivity and Unexpected Isomerization in the Inverse Diels-Alder Reaction of Azolyl Dienes

  摘要：

  Hetaryl-substituted dienamines (la-e and 4a-c) of different geometry when treated with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (2) reacted selectively as enamines (i.e. with the Delta 3,4 double bond) to afford the appropriate E or Z (hetarylvinyl)pyridazines (i.e. la-e gave 3a-c, whereas 4a-c afforded 5a-c). Study on the analogous transformation of the 1Z diene ether (6a) revealed that, in apolar solvent, isomerization of the olefinic side chain occurred (3a rather than 5a was obtained). Formation of the trans product 3a was rationalized by a tautomeric equilibrium of the supposed intermediate 7 for which experimental evidence was provided.

  DOI：

  10.1021/jo00120a041