(Z)-diethyl 3-aminoglutaconate | 163891-36-9

• 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)-diethyl 3-aminoglutaconate
• 英文别名: diethyl (Z)-3-(2-cyanoanilino)pent-2-enedioate
• CAS: 163891-36-9
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: BXHMAZMEKFNMMT-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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)-diethyl 3-aminoglutaconate 在 对甲苯磺酸 作用下， 以 氘代二甲亚砜 为溶剂， 生成 (E)-diethyl 3-aminoglutaconate
  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
• 作为产物：
  描述：

  (E)-diethyl 3-aminoglutaconate 在 对甲苯磺酸 作用下， 以 氘代二甲亚砜 为溶剂， 生成 (Z)-diethyl 3-aminoglutaconate
  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

文献信息

• Diethyl acetonedicarboxylate — a precursor for the synthesis of new substituted 4-aminoquinolines and fused 4-aminopyridines
  作者：T. Charvát、M. Potáček、J. Marek

  DOI：10.1007/bf00816102

  日期：1995.3

  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.