1-phenyl-6-imino-2-thioxopurine | 108575-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-phenyl-6-imino-2-thioxopurine
• CAS: 108575-38-8
• 化学式: C₁₁H₉N₅S
• 分子量: 243.292
• InChiKey: FQQGELHAEAQBCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.25
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  硫代异氰酸苯酯 、 5-氨基-1H-咪唑-4-甲腈 以 吡啶 为溶剂， 反应 2.0h， 以37%的产率得到1-phenyl-6-imino-2-thioxopurine
  参考文献：
  名称：

  某些1-取代的-7-烷基-2-硫代嘌呤的合成与反应：6-甲基氨基-7-壬基-2-硫代嘌呤的X射线结构

  摘要：

  通过异硫氰酸酯与1-烷基-4-氨基-5-氰基咪唑3的反应，合成了数个1-取代的-7-烷基-2-硫代嘌呤8,9,10。3用异硫氰酸甲酯处理得到Dimroth重排产物6-甲基氨基-7-烷基-2-硫氧杂嘌呤11。X射线晶体学明确地定义了11的结构。

  DOI：

  10.1002/jhet.5570230319

文献信息

• Synthesis of New 1-Chalcogenapurines by the Reaction of 5-Aminoimidazole-4-carbonitrile with Isochalcogenocyanates
  作者：Hiroatsu Matsumoto、Sumiko Hara、Nobuyuki Nagata、Kazuyoshi Ikeda、Yoshihisa Mizuno

  DOI：10.3987/com-94-6871

  日期：——

  1-Chalcogenapurines[1-thiapurine derivatives (6,12c,d) and 1-selenapurine derivative (15)] and 1-substituted 1,6-dihydro-6-imino-9H-purine-2(3H)-chalcogenone (4a,b, 13) were synthesized by the reaction of 5(4)-aminoimidazole-4(5)-carbonitrile(3)with various isochalcogenocyanates in pyridine. The reaction of 3 with methyl isothiocyanate in pyridine afforded on ly the 1,6-dihydro-1-methyl-6-imino-9H-purine-2(3H)-thione (4a). On the other hand, the reactions of 3 with ethoxycarbonyl isothiocyanate, benzoyl isothiocyanate or benzhydryl isoselenocyanate preferentially gave the 1-chalcogenapurine derivatives (12c,d, 15), In turn, both 1,6-dihydro-1-phenyl-6-imino-9H-purine-2(3H)-thione (4b) and 6,9-dihydro-2-phenylamino-6-(3-phenylthioureido)imino-1-thiapurine (6) were produced by the reaction of 3 with phenyl isothiocyanate. Modes of cyclization reactions involving 3 and isochalcogenocyanate (R-N=C=X, X; S,Se) depend in remarkable extent on the chalcogene atom as well as R portion of R-N=C=X.