(Z)-3-(2-Cyano-5-methyl-phenylamino)-pent-2-enedioic acid diethyl ester | 163891-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(2-Cyano-5-methyl-phenylamino)-pent-2-enedioic acid diethyl ester
• 英文别名: diethyl (Z)-3-(2-cyano-5-methylanilino)pent-2-enedioate
• CAS: 163891-37-0
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: SJPFVKCOODDAAR-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88.42
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-Cyano-5-methyl-phenylamino)-pent-2-enedioic acid diethyl ester 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以58%的产率得到4-amino-3-ethoxycarbonyl-2-ethoxycarbonylmethyl-7-methylquinoline
  参考文献：
  名称：

  Diethyl acetonedicarboxylate — a precursor for the synthesis of new substituted 4-aminoquinolines and fused 4-aminopyridines

  摘要：

  The reaction of cyclic enaminonitriles 1 with diethyl acetonedicarboxylate (2) affords fused 4-amino-3-ethoxycarbonyl-2-ethoxycarbonylmethyl-pyridines 4. The course of the reaction and the yield of cyclic products were promoted by tin(IV)chloride. N-substituted diethyl 3-aminoglutaconates 3 seem to be intermediates of the cyclization reaction.

  DOI：

  10.1007/bf00816102
• 作为产物：
  描述：

  (E)-3-(2-Cyano-5-methyl-phenylamino)-pent-2-enedioic acid diethyl ester 在 对甲苯磺酸 作用下， 以 氘代二甲亚砜 为溶剂， 生成 (Z)-3-(2-Cyano-5-methyl-phenylamino)-pent-2-enedioic acid diethyl ester
  参考文献：
  名称：

  Isomerization of N-aryl substituted diethyl 3-aminoglutaconates. Part I

  摘要：

  Diethyl acetonedicarboxylate 1 under acid catalysis reacts with aromatic amines and 2-aminonitriles 2 forming N-aryl substituted diethyl 3-aminoglutaconates 3. The structures of the products 3 were studied both in the solid and the liquid state. The presence of the double bond permits two isomeric forms. These E and Z isomers can interchange with one another under catalysis by either an acid or a base in a suitable solvent. The isomeric equilibriums were studied by H-1 NMR spectroscopy with respect to dependence on the polarity of the solvent, the temperature and the substitution present on the aromatic skeleton.

  DOI：

  10.1016/0022-2860(95)09135-1