2-(4-oxo-3,4-dihydrothieno[3,2-b]pyrimidin-2-ylmethyl)benzoic acid | 1146577-77-6

• 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-(4-oxo-3,4-dihydrothieno[3,2-b]pyrimidin-2-ylmethyl)benzoic acid
• 英文别名: 2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-ylmethyl)benzoic acid；o-(4-Oxo-3,4-dihydrothienopyrimidin-2-ylmethyl)benzoic acid；2-[(4-oxo-3H-thieno[3,2-d]pyrimidin-2-yl)methyl]benzoic acid
• CAS: 1146577-77-6
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: TZTGPXZGSQTMEF-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C(Solvent: Acetic acid)
• 沸点：
  539.1±60.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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-(4-oxo-3,4-dihydrothieno[3,2-b]pyrimidin-2-ylmethyl)benzoic acid 在 乙酸酐 作用下， 以92%的产率得到4H-thieno[2',3':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：

  4-tetrahydro-1H-1-pyrrolyl-11H-thieno[2',3':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-(4-oxo-3,4-dihydrothieno[3,2-b]pyrimidin-2-ylmethyl)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

• Condensed isoquinolines. 35*. Synthesis and reactions of 4h-thieno[3′,4′:5,6]pyrimido-[1,2-b]isoquinoline-4,11(5H)-dione
  作者：A. V. Zadorozhny、V. A. Kovtunenko、A. V. Turov

  DOI：10.1007/s10593-010-0608-9

  日期：2010.12

  Derivatives of the previously unknown tetracyclic system 4H-thieno[3',4':5,6] pyrimido[1,2-b]isoquinoline- 4,11(5H)-dione have been synthesized. A comparison of the spectral characteristics and the biological activities of these compounds has been carried out, and also of their positional isomers and benzene isosteres. The differences, associated with the position of the sulfur atom, are most reflected in their electronic spectra.
• 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.