2-amino-5,6-dimethoxy-8H-indeno[2,1-b]thiophene-3-carbonitrile | 1356828-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-amino-5,6-dimethoxy-8H-indeno[2,1-b]thiophene-3-carbonitrile
• 英文别名: 2-amino-6,7-dimethoxy-4H-indeno[2,1-b]thiophene-1-carbonitrile
• CAS: 1356828-58-4
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: KFUXBKOCJQZBOC-UHFFFAOYSA-N

物化性质

• 熔点：
  231-233 °C
• 沸点：
  500.7±50.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5,6-dimethoxy-8H-indeno[2,1-b]thiophene-3-carbonitrile 在 乙酸酐 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4,9-dihydro-4-imino-6,7-dimethoxy-3H-indeno-[1',2':4,5]thieno[2,3-d]pyrimidin-3-amine
  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
• 作为产物：
  描述：

  2-(1,2-dihydro-5,6-dimethoxyinden-3-ylidene)malononitrile 在 sulfur 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 以75%的产率得到2-amino-5,6-dimethoxy-8H-indeno[2,1-b]thiophene-3-carbonitrile
  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