methyl 6-(2-chloro-3,4-dioxocyclobut-1-enyl)-5-methylthieno[3,2-b]thiophene-2-carboxylate | 515880-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: methyl 6-(2-chloro-3,4-dioxocyclobut-1-enyl)-5-methylthieno[3,2-b]thiophene-2-carboxylate
• 英文别名: methyl 3-(2-chloro-3,4-dioxocyclobuten-1-yl)-2-methylthieno[3,2-b]thiophene-5-carboxylate
• CAS: 515880-66-7
• 化学式: C₁₃H₇ClO₄S₂
• 分子量: 326.781
• InChiKey: RXVFUNITSMQDLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,5-二甲基噻吩 、 methyl 6-(2-chloro-3,4-dioxocyclobut-1-enyl)-5-methylthieno[3,2-b]thiophene-2-carboxylate 在 三氯化铝 作用下， 以 正庚烷 、 1,2-二氯乙烷 为溶剂， 以64%的产率得到3-(2,5-dimethyl-3-thienyl)-4-(5-methoxycarbonyl-2-methylthieno[3,2-b]thiophen-3-yl)cyclobutene-1,2-dione
  参考文献：
  名称：

  摘要：

  A procedure was developed for the synthesis of symmetrical and unsymmetrical cyclobutene-1,2-dione derivatives bearing thiophene and thieno[3,2-b]thiophene substituents by the Friedel-Crafts reaction of the corresponding heterocyclic compounds with squaric acid dichloride in the presence of AlCl3 In addition to the target dihetaryl-cyclobutenediones, monoacylation products of methyl (2,5-dimethylthiophen-3-yl)acetate and methyl 5-methylthieno[3,2-blthiophene-2-carboxylate with squaric acid dichloride were isolated and characterized.

  DOI：

  10.1023/a:1020975326034
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 methyl 5-methylthieno[3,2-b]thiophene-2-carboxylate 在 三氯化铝 作用下， 以 正庚烷 、 1,2-二氯乙烷 为溶剂， 以52%的产率得到methyl 6-(2-chloro-3,4-dioxocyclobut-1-enyl)-5-methylthieno[3,2-b]thiophene-2-carboxylate
  参考文献：
  名称：

  摘要：

  A procedure was developed for the synthesis of symmetrical and unsymmetrical cyclobutene-1,2-dione derivatives bearing thiophene and thieno[3,2-b]thiophene substituents by the Friedel-Crafts reaction of the corresponding heterocyclic compounds with squaric acid dichloride in the presence of AlCl3 In addition to the target dihetaryl-cyclobutenediones, monoacylation products of methyl (2,5-dimethylthiophen-3-yl)acetate and methyl 5-methylthieno[3,2-blthiophene-2-carboxylate with squaric acid dichloride were isolated and characterized.

  DOI：

  10.1023/a:1020975326034