2-(5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)benzoic acid | 683779-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-(5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)benzoic acid
• 英文别名: 2-[(5,6-dimethyl-4-oxo-3H-thieno[2,3-d]pyrimidin-2-yl)methyl]benzoic acid
• CAS: 683779-79-5
• 化学式: C₁₆H₁₄N₂O₃S
• 分子量: 314.365
• InChiKey: ORCFCEHUDVGYMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)benzoic acid 在 乙酸酐 作用下， 反应 4.0h， 以90%的产率得到2,3-dimethyl-4H-thieno[3',2':5,6]pyrimido[1,2-b]isoquinoline-4,11(5H)-dione
  参考文献：
  名称：

  Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

  摘要：

  Treatment of 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and-[3,2-d]pyrimidin-2-ylmethyl)benzoic acids and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid with acetic anhydride gave thieno[3',2':5,6]-and-[2',3':5,6]pyrimido[1,2-b]isoquinoline-4,11-diones and isoquino[2,3-a]quinazoline-5,12-dione respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone part of the bicycle.

  DOI：

  10.1007/s10593-008-0119-0
• 作为产物：
  描述：

  2,3-dimethyl-4-tetrahydro-1H-1-pyrrrolyl-11H-thieno[3',2':5,6]pyrimido[1,2-b]isoquinolin-11-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到2-(5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines

  摘要：

  A study was carried out on the nucleophilic cleavage of the lactam bond in 4-amino(pyrrolidino, piperidino, morpolino)thieno[2,3-d]-, -[3,2-d]-, and -[3,4-d]pyrimido[1,2-b]isoquinolin-11-ones. This bond is readily cleaved upon heating in methanolic NaOH at reflux for 1-2 h to give previously unreported 4-amino-2-(o-carboxyphenylmethyl)thienopyrimidines. Replacement of the amine group by an OH group is possible under the reaction conditions, leading to the corresponding, already reported 2-(o-carboxyphenylmethyl)-4-oxothienopyrimidines. Prolonged refluxing (8-12 h) resulted in oxothienopyrimidines as the major products of the transformations of all the thienopyrimido-isoquinolinones studied. Biological activity predictions of these new products were compared in silico.

  DOI：

  10.1007/s10593-012-1095-y

文献信息

• Positional isomers of thienopyrimidinones
  作者：T. T. Kucherenko、A. V. Zadorozhny、V. A. Kovtunenko

  DOI：10.1007/s10593-008-0100-y

  日期：2008.6

  Condensation of o-cyanomethylbenzoic acids with esters of 2-aminothiophene-3-carboxylic and 3-amino-thiophene-2-carboxylic acids to give isomeric 2-(4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylmethyl)-benzoic acids and their ethyl and phenacyl esters. Methylation of esters occurs at N-3. The spectroscopic characteristics of the positional isomers are compared at the level of carboxylic acids, their esters, and methylated products.
• Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives
  作者：A. V. Zadorozhny、V. A. Kovtunenko、A. V. Turov、T. T. Kucherenko

  DOI：10.1007/s10593-008-0119-0

  日期：2008.7

  Treatment of 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and-[3,2-d]pyrimidin-2-ylmethyl)benzoic acids and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid with acetic anhydride gave thieno[3',2':5,6]-and-[2',3':5,6]pyrimido[1,2-b]isoquinoline-4,11-diones and isoquino[2,3-a]quinazoline-5,12-dione respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone part of the bicycle.
• Synthesis of substituted 4-aminothieno[2,3-d]-, 4-aminothieno[3,2-d]- and 4-aminothieno[3,4-d]pyrimidines
  作者：A. V. Zadorozhny

  DOI：10.1007/s10593-012-1095-y

  日期：2012.10

  A study was carried out on the nucleophilic cleavage of the lactam bond in 4-amino(pyrrolidino, piperidino, morpolino)thieno[2,3-d]-, -[3,2-d]-, and -[3,4-d]pyrimido[1,2-b]isoquinolin-11-ones. This bond is readily cleaved upon heating in methanolic NaOH at reflux for 1-2 h to give previously unreported 4-amino-2-(o-carboxyphenylmethyl)thienopyrimidines. Replacement of the amine group by an OH group is possible under the reaction conditions, leading to the corresponding, already reported 2-(o-carboxyphenylmethyl)-4-oxothienopyrimidines. Prolonged refluxing (8-12 h) resulted in oxothienopyrimidines as the major products of the transformations of all the thienopyrimido-isoquinolinones studied. Biological activity predictions of these new products were compared in silico.