1-(1-phenyl-1H-tetrazol-5-yl)-2-(1H-pyrrol-2-yl)ethanone oxime | 1262311-45-4

• 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-(1-phenyl-1H-tetrazol-5-yl)-2-(1H-pyrrol-2-yl)ethanone oxime
• CAS: 1262311-45-4
• 化学式: C₁₃H₁₂N₆O
• 分子量: 268.278
• InChiKey: RBVJUKUHXNTOBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91.98
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(1-phenyl-1H-tetrazol-5-yl)-2-(1H-pyrrol-2-yl)ethanone oxime 在 aluminum amalgam 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 1-(1-phenyl-1H-tetrazol-5-yl)-2-(1H-pyrrol-2-yl)ethanamine
  参考文献：
  名称：

  A hetero-Diels–Alder approach to functionalized 1H-tetrazoles: synthesis of tetrazolyl-1,2-oxazines, -oximes and 5-(1-aminoalkyl)-1H-tetrazoles

  摘要：

  This work describes the first and unprecedented examples of inverse electron demand Diels-Alder reactions of 5-(1-nitrosovinyl)-1-phenyl-1H-tetrazole, generated in situ from the corresponding bromooxime, with electron rich alkenes and heterocycles, providing in good overall yields tetrazolyl,2-oxazines and -oximes. Upon subsequent reduction these allowed the access to 5-(1-aminoalkyl)-1H-tetrazoles, paving the way for a new entry into this important class of compounds, bioisosteres of alpha-amino acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.095
• 作为产物：
  描述：

  吡咯 、 5-(2-bromo-1-hydroxyiminoethyl)-1H-1-phenyltetrazole 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以70%的产率得到1-(1-phenyl-1H-tetrazol-5-yl)-2-(1H-pyrrol-2-yl)ethanone oxime
  参考文献：
  名称：

  A hetero-Diels–Alder approach to functionalized 1H-tetrazoles: synthesis of tetrazolyl-1,2-oxazines, -oximes and 5-(1-aminoalkyl)-1H-tetrazoles

  摘要：

  This work describes the first and unprecedented examples of inverse electron demand Diels-Alder reactions of 5-(1-nitrosovinyl)-1-phenyl-1H-tetrazole, generated in situ from the corresponding bromooxime, with electron rich alkenes and heterocycles, providing in good overall yields tetrazolyl,2-oxazines and -oximes. Upon subsequent reduction these allowed the access to 5-(1-aminoalkyl)-1H-tetrazoles, paving the way for a new entry into this important class of compounds, bioisosteres of alpha-amino acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.095