2-(tert-butyl)-5-methylselenazole | 1559070-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类 - 硒唑类
• 英文名称: 2-(tert-butyl)-5-methylselenazole
• 英文别名: 2-Tert-butyl-5-methyl-1,3-selenazole；2-tert-butyl-5-methyl-1,3-selenazole
• CAS: 1559070-12-0
• 化学式: C₈H₁₃NSe
• 分子量: 202.158
• InChiKey: JSNQMFXSRWQCND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-N-(prop-2-ynyl)propionamide 在 五氯化磷 、 哌啶乙酸盐 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 2-(tert-butyl)-5-methylselenazole
  参考文献：
  名称：

  Synthesis of Selenazoles by in Situ Cycloisomerization of Propargyl Selenoamides Using Oxygen–Selenium Exchange Reaction

  摘要：

  Herein, we describe an approach toward selenazole preparation based on the cycloisomerization of propargyl selenoamides. The selenoamides were synthesized in situ using the Ishihara reagent with spontaneous cyclization to form the 2,5-disubstituted selenazoles. Heterocylcles 9a-j were prepared using readily available starting materials, and yields ranged from moderate to good (20-80%). Methylselenazole 9a could be transformed into a bromomethyl derivative 13 using NBS. The intermediate 13 would provide a more versatile building block for further derivatizations, e.g., the cyanide 14.

  DOI：

  10.1021/jo402661b

文献信息

• Synthesis of Selenazoles by in Situ Cycloisomerization of Propargyl Selenoamides Using Oxygen–Selenium Exchange Reaction
  作者：Chiara Pizzo、S. Graciela Mahler

  DOI：10.1021/jo402661b

  日期：2014.2.21

  Herein, we describe an approach toward selenazole preparation based on the cycloisomerization of propargyl selenoamides. The selenoamides were synthesized in situ using the Ishihara reagent with spontaneous cyclization to form the 2,5-disubstituted selenazoles. Heterocylcles 9a-j were prepared using readily available starting materials, and yields ranged from moderate to good (20-80%). Methylselenazole 9a could be transformed into a bromomethyl derivative 13 using NBS. The intermediate 13 would provide a more versatile building block for further derivatizations, e.g., the cyanide 14.