2-imino-2-morpholinoacetonitrile | 98197-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-imino-2-morpholinoacetonitrile
• 英文别名: imino-morpholino-acetonitrile；morpholine-4-carboximidoyl cyanide
• CAS: 98197-10-5
• 化学式: C₆H₉N₃O
• 分子量: 139.157
• InChiKey: VSKPWXZAOUMQOV-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  214.0±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-imino-2-morpholinoacetonitrile 、 六氟丙酮 以 乙醚 为溶剂， 生成 2,5-Dihydro-5-imino-4-morpholino-2,2-bis(trifluormethyl)oxazol
  参考文献：
  名称：

  Gruetzmacher, Hansjoerg; Roesky, Herbert W., Chemische Berichte, 1986, vol. 119, # 7, p. 2127 - 2134

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-4-吗啉基-1,2,5-噻二唑 在 四乙基氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到2-imino-2-morpholinoacetonitrile
  参考文献：
  名称：

  摘要：

  The electron-acceptor nitrogen and sulfur atoms in 3,4-disubstituted 1,2,5-thiadiazoles are responsible for much decreased reduction potentials and much increased oxidation potentials of these compounds compared with the corresponding carbocyclic derivatives. The thiadiazole ring is resistant to oxidation, and the reversible electron transfer gives rise to fairly stable radical cations. Reductive stability of the heterocycle depends on the nature of its substituents and on the medium: When nucleofuge substituents are present, two-electron transfer in aprotic media results in heteroring opening with iminonitrile formation, whereas in the presence of two readily leaving groups, the electron transfer induces cleavage of the complete heteroring into inorganic anions.

  DOI：

  10.1023/a:1026155407915

文献信息

• Notes: Reaction of Heterocyclic Cyanoformamidines with Some Primary Amines
  作者：Winfield Zehrung, III、Henry Woodburn

  DOI：10.1021/jo01091a043

  日期：1959.9
• Reaction of Cyanogen with Organic Compounds. XIII. Some Nitrogen Heterocycles¹
  作者：HENRY M. WOODBURN、WINFIELD S. ZEHRUNG

  DOI：10.1021/jo01091a003

  日期：1959.9
• Gruetzmacher, Hansjoerg; Roesky, Herbert W., Chemische Berichte, 1986, vol. 119, # 7, p. 2127 - 2134
  作者：Gruetzmacher, Hansjoerg、Roesky, Herbert W.

  DOI：——

  日期：——
• ——
  作者：E. I. Strunskaya、V. V. Yanilkin、Z. A. Bredikhina、N. V. Nastapova、V. I. Morozov、N. I. Maksimyuk、D. R. Sharafutdinova、A. A. Bredikhin

  DOI：10.1023/a:1026155407915

  日期：——

  The electron-acceptor nitrogen and sulfur atoms in 3,4-disubstituted 1,2,5-thiadiazoles are responsible for much decreased reduction potentials and much increased oxidation potentials of these compounds compared with the corresponding carbocyclic derivatives. The thiadiazole ring is resistant to oxidation, and the reversible electron transfer gives rise to fairly stable radical cations. Reductive stability of the heterocycle depends on the nature of its substituents and on the medium: When nucleofuge substituents are present, two-electron transfer in aprotic media results in heteroring opening with iminonitrile formation, whereas in the presence of two readily leaving groups, the electron transfer induces cleavage of the complete heteroring into inorganic anions.