methyl 3-(3-benzylthioureido)benzo[b]thiophene-2-carboxylate | 1184960-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 3-(3-benzylthioureido)benzo[b]thiophene-2-carboxylate
• 英文别名: methyl 3-(benzylcarbamothioylamino)-1-benzothiophene-2-carboxylate
• CAS: 1184960-24-4
• 化学式: C₁₈H₁₆N₂O₂S₂
• 分子量: 356.469
• InChiKey: KBIMIUNBJSLFOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苄胺 、 methyl 3-isothiocyanato-[1]benzothiophene-2-carboxylate 以 甲苯 为溶剂， 以89%的产率得到methyl 3-(3-benzylthioureido)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Modular access to heterocycles: methyl 3-aminobenzo[b]thiophene-2-carboxylate–thiourea linkage or pyrimidine-4-one-2-thione formation

  摘要：

  Modular conditions for the formation of thioureas or pyrimidine-4-one-2-thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-L-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.

  DOI：

  10.1007/s00706-008-0030-5

文献信息

• Modular access to heterocycles: methyl 3-aminobenzo[b]thiophene-2-carboxylate–thiourea linkage or pyrimidine-4-one-2-thione formation
  作者：Jolanta Rousseau、Vilija Kriščiūnienė、Ilona Rimkevičiūtė、Cyril Rousseau、Virginė Amankavičienė、Algirdas Šačkus、Arnaud Tatibouët、Patrick Rollin

  DOI：10.1007/s00706-008-0030-5

  日期：2009.3

  Modular conditions for the formation of thioureas or pyrimidine-4-one-2-thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-L-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.