(Z)-3-[(ethoxycarbonylmethylthio)mercaptomethylene]-1-methyl-2(3H)-indolizinone | 1289579-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-3-[(ethoxycarbonylmethylthio)mercaptomethylene]-1-methyl-2(3H)-indolizinone
• CAS: 1289579-46-9
• 化学式: C₁₄H₁₅NO₃S₂
• 分子量: 309.41
• InChiKey: IZQVEUXTJXAPAM-OWBHPGMISA-N

物化性质

• 沸点：
  461.4±45.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.61
• 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-[(ethoxycarbonylmethylthio)mercaptomethylene]-1-methyl-2(3H)-indolizinone 、 溴乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成 ethyl 3-ethoxycarbonylmethylthio-5-methyl-4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-1-carboxylate 、 ethyl 3-ethoxycarbonylmethylthio-5-methyl-4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-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
• 作为产物：
  描述：

  二硫化碳 、 1-(ethoxycarbonylmethyl)-2-ethylpyridinium bromide 、 溴乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以46%的产率得到(Z)-3-[(ethoxycarbonylmethylthio)mercaptomethylene]-1-methyl-2(3H)-indolizinone
  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