methyl 2-methyl-3-propionyl-4H-thieno[3,2-b]pyrrole-5-carboxylate | 478239-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: methyl 2-methyl-3-propionyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
• 英文别名: methyl 2-methyl-3-propanoyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
• CAS: 478239-06-4
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: VAYUWNVVJOXPMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 methyl 2-methyl-3-propionyl-4H-thieno[3,2-b]pyrrole-5-carboxylate 在 四氯化锡 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以62%的产率得到methyl 6-acetyl-2-methyl-3-propionyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  摘要：

  The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.

  DOI：

  10.1023/a:1023435605723
• 作为产物：
  描述：

  methyl 2-azido-3-(5'-methyl-2'-thienyl)acrylate 在 三氯化铝 、 1-butyl-3-methylimidazolium heptachlorodialuminate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 methyl 2-methyl-3-propionyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  摘要：

  The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.

  DOI：

  10.1023/a:1023435605723

文献信息

• Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles
  作者：Michael M. Krayushkin、Vladimir N. Yarovenko、Stanislav L. Semenov、Igor V. Zavarzin、Anatoliy V. Ignatenko、Andrey Yu. Martynkin、Boris M. Uzhinov

  DOI：10.1021/ol026705i

  日期：2002.10.1

  [GRAPHICS]The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photochrome was synthesized for the first time.