ethyl 4-(ethylthio)-5-((Z)-1-hydroxy-3-(4-methoxyphenyl)allylidene)-2,6-dioxo-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate | 1262340-50-0

• 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: ethyl 4-(ethylthio)-5-((Z)-1-hydroxy-3-(4-methoxyphenyl)allylidene)-2,6-dioxo-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl (5E)-4-ethylsulfanyl-5-[(E)-1-hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-2,6-dioxo-1-phenylpyridine-3-carboxylate
• CAS: 1262340-50-0
• 化学式: C₂₆H₂₅NO₆S
• 分子量: 479.554
• InChiKey: VDJYTKRTCYGMAA-SAYXDPCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  diethyl 2-((2E,4E)-2-(phenylcarbamoyl)-1-(ethylthio)-3-hydroxy-5-(4-methoxyphenyl)penta-2,4-dienylidene)malonate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以90%的产率得到ethyl 4-(ethylthio)-5-((Z)-1-hydroxy-3-(4-methoxyphenyl)allylidene)-2,6-dioxo-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Efficient synthesis of highly functionalized vinylogous thiol esters

  摘要：

  A series of vinylogous thiol esters 2,3 and 2,6-dioxo-1,2,5,6-tetrahydropyridines (cyclic vinylogous thiol esters) 4 were prepared in high to excellent yields from the tandem reaction of readily available alpha-alkenoylketene diethylthioacetals 1 and diethyl malonate. A plausible mechanism, which involves a base catalyzed retro-Michael ring opening of cyclohexanenes 2 to give vinylogous thiol ester 3, is disclosed. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.129