4-cyano-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-5-olate | 4918-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-cyano-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-5-olate
• 英文别名: 3-Phenylsydnone-4-carbonitrile；4-cyano-3-phenylsydnone；4-cyano-3-phenyl-sydnone；3-Phenyl-sydnon-4-carbonsaeurenitril；4-Cyan-3-phenyl-sydnon；4-cyano-3-phenyloxadiazol-3-ium-5-olate
• CAS: 4918-38-1
• 化学式: C₉H₅N₃O₂
• 分子量: 187.158
• InChiKey: PEWSAICGSIPITP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-cyano-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-5-olate 在 硫化氢 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 3-phenyl-4-thiocarbamoylsydnone
  参考文献：
  名称：

  Zotova,S.A.; Yashunskii,V.G., Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 2258 - 2261

  摘要：

  DOI：
• 作为产物：
  描述：

  4-carbamoyl-3-phenyl-sydnone 在 phosphorus pentoxide 作用下， 以 xylene 为溶剂， 反应 1.0h， 生成 4-cyano-3-phenyl-1,2,3-λ⁵-oxadiazol-3-ium-5-olate
  参考文献：
  名称：

  Zotova,S.A.; Yashunskii,V.G., Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 2258 - 2261

  摘要：

  DOI：

文献信息

• 4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne
  作者：Lucie Plougastel、Oleksandr Koniev、Simon Specklin、Elodie Decuypere、Christophe Créminon、David-Alexandre Buisson、Alain Wagner、Sergii Kolodych、Frédéric Taran

  DOI：10.1039/c4cc03816a

  日期：——

  4-Halogeno-sydnones were found to be efficient dipole partners for the strain promoted click reaction with bicyclo-[6.1.0]-nonyne. This bioorthogonal reaction has been applied to protein labeling.

  4-卤代-悉尼酮被发现是双环[6.1.0]-壬炔进行应变促进点击反应的高效偶极伙伴。这种生物正交反应已被应用于蛋白质标记。

• Catalytic Hydration of Nitriles to Amides with Manganese Dioxide on Silica Gel
  作者：Kwang-Ting Liu、Mei-Hsiu Shih、Hsiau-Wen Huang、Chia-Juei Hu

  DOI：10.1055/s-1988-27684

  日期：——

  Hydration of representative nitriles with silica gel supported manganese dioxide at the reflux temperature of hydrocarbon solvents gives the corresponding amides in good to excellent yield. Phenylacetonitrile, however, was partially oxidized to benzoylformamide. Other manganese catalyst systems were also evaluated.

  在烃类溶剂回流温度下，使用硅胶负载的二氧化锰对代表性腈进行水合反应，能够以良好至优异的产率得到相应的酰胺。然而，苯乙腈部分被氧化成了苯甲酰甲酰胺。还评估了其他锰催化体系。
• Synthesis of Sydnone Compounds Having Alternating Carbon-Nitrogen Chain and Heterocyclic Groups at the 4-Position
  作者：Toshio Fuchigami、Mou-Yung Yeh、Takushi Goto、Tsutomu Nonaka、Hsien-Ju Tien

  DOI：10.1246/bcsj.57.116

  日期：1984.1

  carbon-nitrogen chain groups such as 3-aryl-4-(arylcarbonimidoylcarbamoyl)sydnones, 3-aryl-4-(dimethylaminomethylenecarbamoyl)sydnones, and 4-(dimethylaminomethylenethiocarbamoyl)-3-phenylsydnone were prepared in high yields from 3-aryl-4-chloroformylsydnone, 3-aryl-4-carbamoylsydnone, and 3-phenyl-4-thiocarbamoylsydnone, respectively. The cyclization of the alternating carbon-nitrogen chain groups provided

  以高收率制备了具有交替碳氮链基团的全新类型 sydnones，如 3-aryl-4-(arylcarbonimidoylcarbamoyl)sydnones、3-aryl-4-(二甲氨基亚甲基氨基甲酰基)sydnones 和 4-(二甲氨基亚甲基硫代氨基甲酰基)-3-phenylsydnones分别来自 3-aryl-4-chloroformylsydnone、3-aryl-4-carbamoylsydnone 和 3-phenyl-4-thiocarbamoylsydnone。交替碳-氮链基团的环化提供了具有杂环取代基如 1,2,4-恶二唑-5-基、1,2,4-三唑-3-基和 1,2,4-噻二唑-5-基基团的产率很高。
• Convenient and Efficient Synthesis of Pyrazole-Based DHODase Inhibitors from 3-Aryl-4-cyanosydnone
  作者：Fung Wong、Mou-Yung Yeh、En-Ming Chang、Tse-Hsin Chen、En-Chiuan Chang

  DOI：10.1055/s-2006-939041

  日期：——

  Pyrazole-based DHODase inhibitors have been efficient and conveniently synthesized in 51-60% yield from 3-(p-aryl)-4-cyanosydnone via regioselective 1,3-diploar cycloaddition followed by an amidation and a Ritter reaction.

  以 3-（对芳基）-4-氰基ydnone 为原料，通过区域选择性 1,3-二环加成，然后进行酰胺化反应和里特反应，高效、方便地合成了吡唑类 DHOD 酶抑制剂，收率为 51-60%。
• Preparation of Sydnone-4-carboxamide Oximes and Their Conversion into 4-(1,2,4-Oxadiazol-3-yl)sydnones
  作者：Mou-Yung Yeh、Tsutomu Nonaka、Takushi Goto、Ming-Ching Hsu、Toshio Fuchigami、Hsien-Ju Tien

  DOI：10.1246/bcsj.56.3535

  日期：1983.11

  3-Arylsydnone-4-carboxamide oximes (2) were prepared from the corresponding 3-arylsydnone-4-carbonitriles and hydroxylamine in high yields. The amide oximes 2 reacted with orthoesters to give 3-aryl-4-(1,2,4-oxadiazol-3-yl)sydnones.

  由相应的3-芳基苯乙烯酮-4-甲腈和羟胺以高产率制备3-芳基苯乙烯酮-4-甲酰胺肟(2)。酰胺肟2与原酸酯反应得到3-芳基-4-(1,2,4-恶二唑-3-基)苯乙烯酮。