3,4-dihydro-2-(methylthio)-4-oxoquinazoline-3-acetic acid ethyl ester | 13082-21-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4-dihydro-2-(methylthio)-4-oxoquinazoline-3-acetic acid ethyl ester
• 英文别名: ethyl (2-methylthio-4-oxo-3-quinazolinyl)acetate；(2-methylsulfanyl-4-oxo-4H-quinazolin-3-yl)-acetic acid ethyl ester；2-(methylthio)-4-oxo-3(4H)-quinazolineacetic acid, ethyl ester；2-Methylmercapto-4-oxo-3-aethoxycarbonylmethyl-3,4-dihydro-chinazolin；Ethyl 2-(2-methylsulfanyl-4-oxoquinazolin-3-yl)acetate
• CAS: 13082-21-8
• 化学式: C₁₃H₁₄N₂O₃S
• 分子量: 278.332
• InChiKey: JIQDBOFNHHXNFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙基N-[二(甲硫基)亚甲基]甘氨酸酯 、 2-氨基苯甲酸乙酯 在 溶剂黄146 作用下， 反应 4.0h， 以73%的产率得到3,4-dihydro-2-(methylthio)-4-oxoquinazoline-3-acetic acid ethyl ester
  参考文献：
  名称：

  N-[bis(methylthio)methylene]amino Ester (BMMA): Novel Reagents for Annelation of Pyrimidine Moieties

  摘要：

  New reagents for heterocyclic annelations containing a N-[bis(methylthio)methylene]amino moiety (=BMMA) were developed and studied regarding their scope and limitations: one-pot reaction with (hetero)aromatic ortho-aminocarbonyl-type model compounds (''carbonyl'' = COOEt, COMe and CN) to a series of new benzo- or thieno-condensed pyrimidines, pyrrolo[1,2-c]pyrimidines, imidazo[1,2-c]pyrimidines and 1,2,4-triazolo[1,5-c]pyrimidines, depending on the reagent used [(MeS)(2)C=N-R with R = CH2-COOEt, CH(2)CH(2)COOEt, NH-COOEt].

  DOI：

  10.3987/com-94-s86

文献信息

• Regioselective synthesis of N ₍₃₎ ‐ and O‐acylmethyl derivatives of 2‐methylthio‐4(3 <i>H</i> )‐quinazolinone
  作者：Milda M. Burbuliene、Rita Mazeikaite、Povilas Vainilavicius

  DOI：10.1002/jhet.5570450250

  日期：2008.3

  Abstractmagnified imageReaction of 2‐methylthio‐4(3H)‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N(3)‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3H)‐quinazolinone under various conditions to give a mixture of N(3)/O‐isomers.
• Sauter Fritz, Froehlich Johannes, Blasl Karin, Gewald Karl, Heterocycles, 40 (1995) N 2, S 851-866
  作者：Sauter Fritz, Froehlich Johannes, Blasl Karin, Gewald Karl

  DOI：——

  日期：——
• N-[bis(methylthio)methylene]amino Ester (BMMA): Novel Reagents for Annelation of Pyrimidine Moieties
  作者：Fritz Sauter、Johannes Fröhlich、Krain Blasl、Karl Gewald

  DOI：10.3987/com-94-s86

  日期：——

  New reagents for heterocyclic annelations containing a N-[bis(methylthio)methylene]amino moiety (=BMMA) were developed and studied regarding their scope and limitations: one-pot reaction with (hetero)aromatic ortho-aminocarbonyl-type model compounds (''carbonyl'' = COOEt, COMe and CN) to a series of new benzo- or thieno-condensed pyrimidines, pyrrolo[1,2-c]pyrimidines, imidazo[1,2-c]pyrimidines and 1,2,4-triazolo[1,5-c]pyrimidines, depending on the reagent used [(MeS)(2)C=N-R with R = CH2-COOEt, CH(2)CH(2)COOEt, NH-COOEt].