ethyl 1-(p-chlorobenzoyl)-2-[(2-ethoxycarbonylethyl)thio]-6,8-dimethylindolizine-3-carboxylate | 1017251-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-(p-chlorobenzoyl)-2-[(2-ethoxycarbonylethyl)thio]-6,8-dimethylindolizine-3-carboxylate
• 英文别名: Ethyl 1-(4-chlorobenzoyl)-2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-3-carboxylate；ethyl 1-(4-chlorobenzoyl)-2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-3-carboxylate
• CAS: 1017251-99-8
• 化学式: C₂₅H₂₆ClNO₅S
• 分子量: 488.004
• InChiKey: AAFJJTLZMIRQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-(p-chlorobenzoyl)-2-[(2-ethoxycarbonylethyl)thio]-6,8-dimethylindolizine-3-carboxylate 、 溴乙酸乙酯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 以88%的产率得到diethyl 3-(p-chlorophenyl)-4,6-dimethylthieno[3,2-a]indolizine-2,9-dicarboxylate
  参考文献：
  名称：

  First Ring Contraction-Desulfurization of 1-(Arylcarbonyl)pyrido[2,1-c]-1,4-thiazines to 1-(Arylcarbonyl)indolizines and Its Application to 3-Arylthieno[3,2-a]indolizine Synthesis

  摘要：

  The ring contraction-desulfurization route from transient 1-(arylcarbonyl)pyridol2,1-c]-1,4-thiazine intermediates, generated in situ from the treatment of the corresponding pyridinium salts with a base and then a dehydrogenation agent, to 1-(arylcarbonyl)indolizines was first observed. By using this route three 1-arylcarbonyl-6,8-dimethylindolizines having the protected 2-thiol group were prepared and their transformation to 2-acyl-3-arylthieno[3,2-a]indolizine derivatives were performed in good yields.

  DOI：

  10.3987/com-07-s(w)30
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 四氯苯醌 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成 ethyl 1-(p-chlorobenzoyl)-2-[(2-ethoxycarbonylethyl)thio]-6,8-dimethylindolizine-3-carboxylate
  参考文献：
  名称：

  First Ring Contraction-Desulfurization of 1-(Arylcarbonyl)pyrido[2,1-c]-1,4-thiazines to 1-(Arylcarbonyl)indolizines and Its Application to 3-Arylthieno[3,2-a]indolizine Synthesis

  摘要：

  The ring contraction-desulfurization route from transient 1-(arylcarbonyl)pyridol2,1-c]-1,4-thiazine intermediates, generated in situ from the treatment of the corresponding pyridinium salts with a base and then a dehydrogenation agent, to 1-(arylcarbonyl)indolizines was first observed. By using this route three 1-arylcarbonyl-6,8-dimethylindolizines having the protected 2-thiol group were prepared and their transformation to 2-acyl-3-arylthieno[3,2-a]indolizine derivatives were performed in good yields.

  DOI：

  10.3987/com-07-s(w)30