2-(p-chlorophenylamino)-3-(p-chlorophenyl)-4(3H)-quinazolinone | 19801-32-2

• 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: 2-(p-chlorophenylamino)-3-(p-chlorophenyl)-4(3H)-quinazolinone
• 英文别名: 2-(4-chloro-anilino)-3-(4-chloro-phenyl)-3H-quinazolin-4-one；3-(4-Chlorphenyl)-2-(4-chloranilino)-3,4-dihydro-chinazolin-4-on；2-(4-Chloroanilino)-3-(4-chlorophenyl)quinazolin-4-one
• CAS: 19801-32-2
• 化学式: C₂₀H₁₃Cl₂N₃O
• 分子量: 382.249
• InChiKey: XUAWEHUPPPZXJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2-碘苯胺 、 双(4-氯苯基)碳二亚胺 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、2.07 MPa 条件下， 反应 24.0h， 以75%的产率得到2-(p-chlorophenylamino)-3-(p-chlorophenyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Palladium-Catalyzed Cyclocarbonylation of o-Iodoanilines with Heterocumulenes:  Regioselective Preparation of 4(3H)-Quinazolinone Derivatives

  摘要：

  A catalyst system comprising palladium acetate-bidentate phosphine is effective for the cyclocarbonylation of o-iodoanilines with heterocumulenes at 70-100 degrees C for 12-24 h to give the corresponding 4(3H)-quinazolinone derivatives in good yields. Utilizing o-iodoaniline with isocyanates, carbodiimides, and ketenimines for the reaction, 2,4-( LH,3H)-quinazolinediones, 2-amino4(3H)-quinazolinones and 2-alkyl-4(3H)-quinazolinones were obtained, respectively. The nature of the substrates including the electrophilicity of the carbon center of the carbodiimide, and the stability of the ketenimine, influence the product yields of this reaction. Urea-type intermediates are believed to be generated first in situ from the reaction of o-iodoanilines with heterocumulenes, followed by palladium-catalyzed carbonylation and cyclization to yield the products.

  DOI：

  10.1021/jo991922r

文献信息

• Palladium-Catalyzed Cyclocarbonylation of <i>o</i>-Iodoanilines with Heterocumulenes:  Regioselective Preparation of 4(3<i>H</i>)-Quinazolinone Derivatives
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo991922r

  日期：2000.5.1

  A catalyst system comprising palladium acetate-bidentate phosphine is effective for the cyclocarbonylation of o-iodoanilines with heterocumulenes at 70-100 degrees C for 12-24 h to give the corresponding 4(3H)-quinazolinone derivatives in good yields. Utilizing o-iodoaniline with isocyanates, carbodiimides, and ketenimines for the reaction, 2,4-( LH,3H)-quinazolinediones, 2-amino4(3H)-quinazolinones and 2-alkyl-4(3H)-quinazolinones were obtained, respectively. The nature of the substrates including the electrophilicity of the carbon center of the carbodiimide, and the stability of the ketenimine, influence the product yields of this reaction. Urea-type intermediates are believed to be generated first in situ from the reaction of o-iodoanilines with heterocumulenes, followed by palladium-catalyzed carbonylation and cyclization to yield the products.