3,9-dihydro-6,7-dimethoxy-2-phenyl-4H-indeno-[1',2':4,5]thieno[2,3-d]pyrimidin-4-one | 1356828-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 3,9-dihydro-6,7-dimethoxy-2-phenyl-4H-indeno-[1',2':4,5]thieno[2,3-d]pyrimidin-4-one
• 英文别名: 3,9-Dihydro-6,7-dimethoxy-2-phenyl-4h-indeno[1',2':4,5]thieno[2,3-d]pyrimidin-4-one；13,14-dimethoxy-5-phenyl-8-thia-4,6-diazatetracyclo[7.7.0.02,7.011,16]hexadeca-1(9),2(7),5,11,13,15-hexaen-3-one
• CAS: 1356828-69-7
• 化学式: C₂₁H₁₆N₂O₃S
• 分子量: 376.436
• InChiKey: NANLQHQBKUTTBB-UHFFFAOYSA-N

物化性质

• 熔点：
  308-310 °C
• 沸点：
  605.3±65.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-amino-5,6-dimethoxy-8H-indeno[2,1-b]thiophene-3-carbonitrile 在 硫酸 、 溶剂黄146 作用下， 反应 8.0h， 生成 3,9-dihydro-6,7-dimethoxy-2-phenyl-4H-indeno-[1',2':4,5]thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Expedient approach for the synthesis of novel indenothiophene derivatives

  摘要：

  Gewald reaction of 2-(2,3-dihydro-5,6-dimethoxy-1H-inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H2SO4 furnished the expected 2-amino-3-carboxamide derivative instead of the corresponding carboxylic acid. The key intermediates 2-aminoindenothiophene-3-carbonitrile and -3-carboxamide were used for the synthesis of tetracyclic indenothienopyrimidine derivatives by cyclocondensation reaction with acid chlorides, amides, formic acid, or hydrazine hydrate. Neat reactions of the carbonitrile with cyclic and aliphatic ketones in the presence of anhydrous ZnCl2 furnished pentacyclic and tetracyclic indenothienopyridine derivatives, respectively, in good yields. All new compounds were characterized by spectroscopic and analytical data.

  DOI：

  10.1007/s00706-011-0657-5