5-(4-Methoxyphenylmethylene)-2-morpholino-2-thiazolin-4-one | 36937-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-Methoxyphenylmethylene)-2-morpholino-2-thiazolin-4-one
• 英文别名: 5-p-Methoxybenzyliden-2-morpholino-2-thiazolin-4-on；5-(4-methoxy-benzylidene)-2-morpholin-4-yl-thiazol-4-one；5-[(4-Methoxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one
• CAS: 36937-45-8
• 化学式: C₁₅H₁₆N₂O₃S
• mdl: MFCD00553317
• 分子量: 304.37
• InChiKey: MHBMVJNVTAPDMF-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: ethanol (64-17-5))
• 沸点：
  485.0±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Methoxyphenylmethylene)-2-morpholino-2-thiazolin-4-one 在 sodium 、 苯甲酰乙酸乙酯 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以32%的产率得到5-(4-methoxyphenylmethylidene)-2'-morpholin-4-yl-2,5'-bithiazolylidene-4,4'-dione
  参考文献：
  名称：

  Reactions of N,N-Disubstituted 5-Arylmethylidene-2-amino-thiazol-4(5H)-ones with CH Acids

  摘要：

  N,N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5H)-ones reacted with diethyl malonate, ethyl benzoylacetate, acetylacetone, or cyclopentadiene in refluxing toluene and in presence of powdered sodium to give the respective 5-arylmethylidene-2'-amino-2,5'-bithiazolylidene-4,4'-dione derivatives in moderate yields. 5-Benzylidene-2-morpholin-4-yl-2-thiazol-4(5H)-one reacted with malononitrile in toluene and in presence of powdered sodium under mild conditions to afford the 1:1 adduct, benzylmalononitrile, and 2-morpholin-4-yl-2-thiazol-4(5H)-one. However, similar treatment of 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-one with malononitrile yielded the 2,5'-bithiazolylidene-4,4'-dione derivative together with 4-methoxyphenylmethylidene malononitrile. Treatment of 5-benzylidene- and 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-ones with 3-phenyl-4-oxo-2-thioxo-1,3-thiazolidine in refluxing toluene and in presence of powdered sodium produced 5-arylmethylidene-3-phenyl-4-oxo-2-thioxo-1,3-thiazolidines in good yields. The structures of all products were deduced from microanalytical and spectroscopic data, mechanistic details are discussed.

  DOI：

  10.1007/s007060200092
• 作为产物：
  描述：

  2-硫代-5-(4-甲氧基苄亚基)噻唑烷-4-酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 5-(4-Methoxyphenylmethylene)-2-morpholino-2-thiazolin-4-one
  参考文献：
  名称：

  Omar, M.T.; Sherif, F.A., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 5, p. 835 - 842

  摘要：

  DOI：

文献信息

• Omar, M. T.; Kasem, M. A., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1413 - 1415
  作者：Omar, M. T.、Kasem, M. A.

  DOI：——

  日期：——
• Kandeel, Kamal A.; Youssef, Ali M.; El-Bestawy, Hany M., Journal of Chemical Research, Miniprint, 2003, # 11, p. 1129 - 1140
  作者：Kandeel, Kamal A.、Youssef, Ali M.、El-Bestawy, Hany M.、Omar, Mohamed T.

  DOI：——

  日期：——
• Omar, M.T.; Sherif, F.A., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 5, p. 835 - 842
  作者：Omar, M.T.、Sherif, F.A.

  DOI：——

  日期：——
• Reactions of N,N-Disubstituted 5-Arylmethylidene-2-amino-thiazol-4(5H)-ones with CH Acids
  作者：Kamal A. Kandeel、Ali M. Youssef、Hany M. El-Bestawy、Mohamed T. Omar

  DOI：10.1007/s007060200092

  日期：2002.9.1

  N,N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5H)-ones reacted with diethyl malonate, ethyl benzoylacetate, acetylacetone, or cyclopentadiene in refluxing toluene and in presence of powdered sodium to give the respective 5-arylmethylidene-2'-amino-2,5'-bithiazolylidene-4,4'-dione derivatives in moderate yields. 5-Benzylidene-2-morpholin-4-yl-2-thiazol-4(5H)-one reacted with malononitrile in toluene and in presence of powdered sodium under mild conditions to afford the 1:1 adduct, benzylmalononitrile, and 2-morpholin-4-yl-2-thiazol-4(5H)-one. However, similar treatment of 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-one with malononitrile yielded the 2,5'-bithiazolylidene-4,4'-dione derivative together with 4-methoxyphenylmethylidene malononitrile. Treatment of 5-benzylidene- and 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-ones with 3-phenyl-4-oxo-2-thioxo-1,3-thiazolidine in refluxing toluene and in presence of powdered sodium produced 5-arylmethylidene-3-phenyl-4-oxo-2-thioxo-1,3-thiazolidines in good yields. The structures of all products were deduced from microanalytical and spectroscopic data, mechanistic details are discussed.