ethyl 2-ethoxycarbonylmethylthio-3-hydroxy-4-phenylcyclo[3.2.2]azine-1-carboxylate | 1289579-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 2-ethoxycarbonylmethylthio-3-hydroxy-4-phenylcyclo[3.2.2]azine-1-carboxylate
• CAS: 1289579-93-6
• 化学式: C₂₃H₂₁NO₅S
• 分子量: 423.489
• InChiKey: VEBILULMNKBNKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.24
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  ethyl 3-ethoxycarbonylmethylthio-4-oxo-5-phenyl-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-1-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 2,4,6-三甲基吡啶 为溶剂， 反应 0.25h， 以24%的产率得到ethyl 2-ethoxycarbonylmethylthio-3-hydroxy-4-phenylcyclo[3.2.2]azine-1-carboxylate
  参考文献：
  名称：

  A New Synthetic Approach to Some Functionalized Cycl[3.2.2]azine Derivatives

  摘要：

  Dehydrogenation of some ethyl 4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-1-carboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were examined. No simply dehydrogenated products such as 4-oxo-1H- and 4-oxo-8H-1,4-thiazino[3,4,5-cd]indolizines or their full conjugated enol forms could be obtained, but ethyl cycl[3.2.2]azine-1-carboxylates were directly obtained via the cyclization and the subsequent desulfurization of the 4H-1,4-thiazine ring in the dehydrogenated intermediates.

  DOI：

  10.3987/com-10-s(e)72