5-amino-2-(thiophen-2-yl)oxazole-4-carbonitrile | 909077-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-2-(thiophen-2-yl)oxazole-4-carbonitrile
• 英文别名: 5-amino-4-cyano-2-(2-thienyl)-1,3-oxazole；5-Amino-2-(2-thienyl)-1,3-oxazole-4-carbonitrile；5-amino-2-thiophen-2-yl-1,3-oxazole-4-carbonitrile
• CAS: 909077-40-3
• 化学式: C₈H₅N₃OS
• 分子量: 191.213
• InChiKey: VWTYSDBXQIIJJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-2-(thiophen-2-yl)oxazole-4-carbonitrile 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.25h， 生成 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thiophen-2-yl)oxazole
  参考文献：
  名称：

  Microwave-mediated synthesis and manipulation of a 2-substituted-5-aminooxazole-4-carbonitrile library

  摘要：

  A 2-substituted-5-aminooxazole-4-carbonitrile library has been synthesised and modified via microwave-mediated and flow chemistries. One synthesised compound, 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thien-2-yl)oxazole, contains three distinct heterocycles attached to the central oxazole core, highlighting the structural diversity of this approach. Three oxazoles had micromolar k(i) values against cannabinoid (CB1/CB2) receptors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.081
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 对苯二磺酸氨基丙二酰丁氰 以 N-甲基吡咯烷酮 为溶剂， 以94%的产率得到5-amino-2-(thiophen-2-yl)oxazole-4-carbonitrile
  参考文献：
  名称：

  Microwave-mediated synthesis and manipulation of a 2-substituted-5-aminooxazole-4-carbonitrile library

  摘要：

  A 2-substituted-5-aminooxazole-4-carbonitrile library has been synthesised and modified via microwave-mediated and flow chemistries. One synthesised compound, 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thien-2-yl)oxazole, contains three distinct heterocycles attached to the central oxazole core, highlighting the structural diversity of this approach. Three oxazoles had micromolar k(i) values against cannabinoid (CB1/CB2) receptors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.081

文献信息

• Synthesis and friedländer reactions of 5-amino-4-cyano-1,3-oxazoles
  作者：M CARREIRAS、A ELEUTERIO、C DIAS、M BRITO、D BRITES、J MARCOCONTELLES、E GOMEZSANCHEZ

  DOI：10.1016/s0385-5414(07)81101-4

  日期：2007.10.1

  The synthesis of 2-substituted 5-amino-4-cyano-1,3-oxazoles (1-4, 611) and the Friedlander-type reaction of compounds 1, 3, 4 is described. Compounds 13-17 are tacrine (18) analogues provided by the Friedlander reaction. The anti-cholinesterase activity of compounds 13, 14, 16 and 17 has been investigated.