N-(1-deoxy-2,3,4,6-di-O-isopropylidene-α-L-sorbofuranosyl)-N'-(3-(2-methoxycarbonyl)benzo[b]thiophenyl)thiourea | 1184960-39-1

• 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: N-(1-deoxy-2,3,4,6-di-O-isopropylidene-α-L-sorbofuranosyl)-N'-(3-(2-methoxycarbonyl)benzo[b]thiophenyl)thiourea
• CAS: 1184960-39-1
• 化学式: C₂₃H₂₈N₂O₇S₂
• 分子量: 508.617
• InChiKey: BMUXWTSSWGELRB-VNLSBWRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  96.51
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  1-deoxy-1-amino-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 、 methyl 3-isothiocyanato-[1]benzothiophene-2-carboxylate 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.75h， 以82%的产率得到N-(1-deoxy-2,3,4,6-di-O-isopropylidene-α-L-sorbofuranosyl)-N'-(3-(2-methoxycarbonyl)benzo[b]thiophenyl)thiourea
  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