1-butyl-5-methylselanyl-1H-tetrazole | 1453815-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-butyl-5-methylselanyl-1H-tetrazole
• CAS: 1453815-69-4
• 化学式: C₆H₁₂N₄Se
• 分子量: 219.148
• InChiKey: OLRNIJJWBPJSIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  313.5±25.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  丁基甲酰胺 在 selenium 、 sodium azide 、 三光气 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.0h， 生成 1-butyl-5-methylselanyl-1H-tetrazole
  参考文献：
  名称：

  One-pot synthesis of 1-substituted-5-alkylselanyl-1 H -tetrazoles from isoselenocyanates: unexpected formation of N -alkyl- N -arylcyanamides and ( Z )- Se -alkyl- N -cyano- N , N′ -diarylisoselenoureas

  摘要：

  1-Substituted-5-alkylsulfanyl-1H-tetrazoles are well known class of organic substances with various applications in medicinal chemistry or photographic industry. Their selenium analogues, 1-substituted-5-alkylselanyl-1H-tetrazoles are, however, much less explored because of the lack of suitable methods for their preparation. In this work we investigated the synthesis of 1-alkyl/aryl-5-alkylselanyl-1H-tetrazoles from synthetically available alkyl/arylisoselenocyanates. One-pot reactions of arylisoseleno cyanates with sodium azide and alkylating agent led to the target 5-alkylselanyl-1-aryl-1H-tetrazoles but also to interesting side products, namely N-alkyl-N-arylcyanamides and (2)-Se-alkyl-N-cyano-N,N'-diarylisoselenoureas. Nevertheless, when alkylisoselenocyanates were utilized as the substrates, the reactions led exclusively to the formation of 1-alkyl-5-alkylselanyl-1H-tetrazoles in good yields. This simple one-pot procedure brings new possibilities for the preparation of variously substituted selenium compounds. It also opens the way to further investigations of selenium isosteres of the widely utilized 5-thiotetrazole moiety in biomedical applications. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.103