methyl (2Z)-2-(dimethylamino)-3-phenylpenta-2,4-dienoate | 79841-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2Z)-2-(dimethylamino)-3-phenylpenta-2,4-dienoate
• CAS: 79841-38-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: UWMFKTXZRYKCNW-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-2-(dimethylamino)-3-phenylpenta-2,4-dienoate 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 3-hydroxy-5-methyl-4-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Intramolecular 1,5-Hydride Shift in Products of Stevens 3,2-Rearrangement of Ammonium Salts Containing 3-Phenyl-2-propynyl Group

  摘要：

  In products of Stevens 3,2-rearrangement of ammonium salts containing alongside alkoxycarbony-ymethyl also 3-phenyl-2-propynyl group an intramolecular 1,5-hydride shift is observed resulting in immonium salts which transform into antinoesters of enamine structure. The hydrolysis of the latter provides the lower aliphatic aldehydes and the corresponding aminoesters. An acid treatment of the reaction mixture affords a mixture of hydrogenated and nonhydrogenated esters of alpha-ketoacids originating from the mixture of 1,3-diene antinoesters. At treating, with concn. HCl of the obtained mixture the nonhydrogeneted ketoester undergoes cyclization into 4-methyl-3-phenyl-2-buten-1,4-olide.

  DOI：

  10.1023/b:rujo.0000003157.80528.0a
• 作为产物：
  描述：

  (methoxycarbonylmethyl)dimethyl-(3-phenylprop-2-ynyl)ammonium bromide 在 sodium methylate 作用下， 以 乙醚 为溶剂， 生成 methyl (2Z)-2-(dimethylamino)-3-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Intramolecular 1,5-Hydride Shift in Products of Stevens 3,2-Rearrangement of Ammonium Salts Containing 3-Phenyl-2-propynyl Group

  摘要：

  In products of Stevens 3,2-rearrangement of ammonium salts containing alongside alkoxycarbony-ymethyl also 3-phenyl-2-propynyl group an intramolecular 1,5-hydride shift is observed resulting in immonium salts which transform into antinoesters of enamine structure. The hydrolysis of the latter provides the lower aliphatic aldehydes and the corresponding aminoesters. An acid treatment of the reaction mixture affords a mixture of hydrogenated and nonhydrogenated esters of alpha-ketoacids originating from the mixture of 1,3-diene antinoesters. At treating, with concn. HCl of the obtained mixture the nonhydrogeneted ketoester undergoes cyclization into 4-methyl-3-phenyl-2-buten-1,4-olide.

  DOI：

  10.1023/b:rujo.0000003157.80528.0a