2-(benzylsulfanyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one | 478029-81-1

• 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-(benzylsulfanyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one
• 英文别名: 2-(Benzylsulfanyl)[1]benzothieno[3,2-d]pyrimidin-4-ol；2-benzylsulfanyl-3H-[1]benzothiolo[3,2-d]pyrimidin-4-one
• CAS: 478029-81-1
• 化学式: C₁₇H₁₂N₂OS₂
• 分子量: 324.427
• InChiKey: IOADGBPTDRSNRW-UHFFFAOYSA-N

物化性质

• 沸点：
  542.6±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzylsulfanyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one 、 4-甲氧基苯硼酸 在 copper(I) 2-hydroxy-3-methylbenzoate 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 48.17h， 以59%的产率得到2-(4-methoxyphenyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

  摘要：

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

  DOI：

  10.3987/com-15-s(t)12
• 作为产物：
  描述：

  3-氨基苯并[b]噻吩-2-羧酸甲酯 在 吡啶 、 氨 、 sodium hydride 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 甲苯 为溶剂， -34.0~20.0 ℃ 、200.0 kPa 条件下， 反应 2.0h， 生成 2-(benzylsulfanyl)[1]benzothieno[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

  摘要：

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

  DOI：

  10.3987/com-15-s(t)12

文献信息

• Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions
  作者：Algirdas Šačkus、Vilija Kriščiūnienė、Gita Matulevičiūtė、Osvaldas Paliulis

  DOI：10.3987/com-15-s(t)12

  日期：——

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.