3-(2-methoxyphenyl)-1-methylquinazoline-2,4(1H,3H)-dione | 966-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(2-methoxyphenyl)-1-methylquinazoline-2,4(1H,3H)-dione
• 英文别名: 1-Methyl-3-(2-methoxy-phenyl)-1.2.3.4-tetrahydro-chinazolindion-(2.4)；3-(2-methoxy-phenyl)-1-methyl-1H-quinazoline-2,4-dione；3-(2-Methoxyphenyl)-1-methylquinazoline-2,4-dione
• CAS: 966-08-5
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: DFDHRMZPCWRXCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基苯唑 、 2-(三氟甲基)苯基异氰酸酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 20.0h， 以69%的产率得到3-(2-methoxyphenyl)-1-methylquinazoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Quinazolinediones

  摘要：

  A nickel(0)-catalyzed method for the synthesis of quinazolinediones from isatoic anhydrides and isocyanates is described. High-throughput ligand screening revealed that XANTPHOS was the optimal ligand for this transformation. Subsequent optimization studies, supported by kinetic analysis, significantly expanded the reaction scope. The reaction exhibits a case of substrate inhibition kinetics with respect to the isocyanate. Preliminary results on an asymmetric synthesis of atropisomeric quinazolinediones are reported.

  DOI：

  10.1021/acs.orglett.7b00052

文献信息

• Nickel-Catalyzed Synthesis of Quinazolinediones
  作者：Gregory L. Beutner、Yi Hsiao、Thomas Razler、Eric M. Simmons、William Wertjes

  DOI：10.1021/acs.orglett.7b00052

  日期：2017.3.3

  A nickel(0)-catalyzed method for the synthesis of quinazolinediones from isatoic anhydrides and isocyanates is described. High-throughput ligand screening revealed that XANTPHOS was the optimal ligand for this transformation. Subsequent optimization studies, supported by kinetic analysis, significantly expanded the reaction scope. The reaction exhibits a case of substrate inhibition kinetics with respect to the isocyanate. Preliminary results on an asymmetric synthesis of atropisomeric quinazolinediones are reported.