3-isocyano-5-phenyl-1,2,4-oxadiazole | 479638-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-isocyano-5-phenyl-1,2,4-oxadiazole
• 英文别名: 1,2,4-Oxadiazole, 3-(isocyanomethyl)-5-phenyl-；3-(isocyanomethyl)-5-phenyl-1,2,4-oxadiazole
• CAS: 479638-77-2
• 化学式: C₁₀H₇N₃O
• 分子量: 185.185
• InChiKey: BVYLYLBMVYPXIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-isocyano-5-phenyl-1,2,4-oxadiazole 、 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到3-(5-phenyl-1,2,4-oxadiazol-3-yl)-4H-imidazo[1,5-d]pyrido[2,3-b][1,4]thiazine
  参考文献：
  名称：

  Synthesis of a New Series of Imidazo[1,5-d]pyrido[2,3-b][1,4]thiazines as Potential Ligands for the GABA Receptor Complex

  摘要：

  Starting from 2-chloro-3-nitropyridine, H-1-pyrido[2,3-b][1,4]thiazin-2(3H)-one was synthesized. This compound was reacted with potassium tert-butoxide and diethyl chlorophosphate to give the intermediate H-1-pyrido[2,3-b][1,4]thiazin-2-ylphosphate derivative, which in turn afforded the 1,2,4-oxadiazolylimidazo[1,5-d]pyrido[2,3-b]pyrazine derivatives. The title compounds are potential ligands for the gamma-aminobutyric acid A/benzodiazepine receptor complex.

  DOI：

  10.1007/s007060200091

文献信息

• Studies on the chemistry of thienoannelated<i>O,N</i>- and<i>S,N</i>-containing heterocycles. 24 [1]. Synthesis of imidazo[1,5-<i>d</i>]thieno[2,3-<i>b</i>][1,4]-thiazine derivatives as potential receptor ligands
  作者：Thomas Erker、Norbert Handler

  DOI：10.1002/jhet.5570390407

  日期：2002.7

  A facile synthesis of the imidazo[1,5-d]thieno[2,3-b][1,4]thiazine ring system is described. Reaction of 6-benzyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazine-2-one (1) with potassium tert-butoxide and diethylchlorophosphate gave intermediate 2 which resulted in the disired ring system after adding the corresponding isocyanides and potassium tert-butoxide.

  描述了咪唑并[1,5- d ]噻吩并[2,3- b ] [1,4]噻嗪环系统的简便合成方法。的6-苄基-2,3-二氢-1-反应ħ -噻吩并[2,3- b ] [1,4]噻嗪-2-酮（1）与钾叔丁醇和氯磷酸二乙酯，得到中间体2，其导致加入相应的异氰化物和叔丁醇钾后，形成不想要的环系统。
• Synthesis of a New Series of Imidazo-[1,5-a]pyrido[2,3-e]pyrazines as Potential Ligands for the GABA Receptor Complex
  作者：Manuela Weber、Herbert Bartsch、Thomas Erker

  DOI：10.1007/s007060200037

  日期：2002.5.1

  -butoxide and diethyl chlorophosphate to afford an intermediate dihydropyrido[2,3- b ]pyrazin-2-ylphosphate derivative which in turn furnished the desired 1,2,4-oxadiazolylimidazo[1,5- a ]pyrido[2,3- e ]pyrazine derivatives with 5-alkyl-3-isocyanomethyl-1,2,4-oxadiazoles in the presence of additional tert -butoxide. The title compounds are potential ligands for the γ-aminobutyric acid A/benzodiazepine receptor

  从2-氯-3-硝基吡啶开始，合成2-异丙基-1，4-二氢吡啶并[2，3 - b ]吡嗪-2（ 3H ），3-二酮。将该化合物与 叔 丁醇钾和氯代磷酸二乙酯反应， 得到中间体二氢吡啶并[2,3 - b ]吡嗪-2-基磷酸酯衍生物，进而提供所需的1,2,4-恶二唑基咪唑并[1,5- a ]在另外的 叔 丁醇盐存在下，将吡啶并[2,3- e ]吡嗪衍生物与5-烷基-3-异氰基甲基-1,2,4-恶二唑合成 。标题化合物是γ-氨基丁酸A /苯并二氮杂receptor受体复合物的潜在配体。