6-benzyl-7-thioxo-1,6,7,8-tetrahydro-1,6,8-triazacyclopenta[b]naphthalen-5-one | 1184960-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-benzyl-7-thioxo-1,6,7,8-tetrahydro-1,6,8-triazacyclopenta[b]naphthalen-5-one
• 英文别名: 6-Benzyl-7-thioxo-1,6,7,8-tetrahydro-1,6,8-triaza-cyclopenta[b]naphthalen-5-one；3-benzyl-2-sulfanylidene-1,8-dihydropyrrolo[3,2-g]quinazolin-4-one
• CAS: 1184960-28-8
• 化学式: C₁₇H₁₃N₃OS
• 分子量: 307.376
• InChiKey: SWBGLZAVFYCPBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-benzyl-7-thioxo-1,6,7,8-tetrahydro-1,6,8-triazacyclopenta[b]naphthalen-5-one 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以62%的产率得到1,6-dibenzyl-7-benzylsulfanyl-1,6-dihydro-1,6,8-triazacyclopenta[b]naphthalen-5-one
  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
• 作为产物：
  描述：

  ethyl 6-isothiocyanato-1H-indole-5-carboxylate 、 苄胺 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以72%的产率得到6-benzyl-7-thioxo-1,6,7,8-tetrahydro-1,6,8-triazacyclopenta[b]naphthalen-5-one
  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