2-Phenyl-4-[phenyl(phenylselanyl)methyl]quinazoline | 1612876-04-6

• 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-Phenyl-4-[phenyl(phenylselanyl)methyl]quinazoline
• CAS: 1612876-04-6
• 化学式: C₂₇H₂₀N₂Se
• 分子量: 451.429
• InChiKey: HXUDYSXTYOMFAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-2-phenyl-4-(phenyl(phenylselanyl)methylene)-4H-benzo[d][1,3]oxazine 在 ammonium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以67%的产率得到2-Phenyl-4-[phenyl(phenylselanyl)methyl]quinazoline
  参考文献：
  名称：

  氯化铁/三有机二硒化物促进邻炔基丙二胺的区域和立体选择性环化：( Z）-4-（硫属元素）亚甲基苯并恶嗪的合成

  摘要：

  AbstractIntramolecular 6‐exo‐dig cyclization of ortho‐alkynylanilides has been employed in a regio‐ and stereoselective synthesis of (Z)‐4‐(chalcogen)methylenebenzoxazines. Several reaction parameters were screened for the efficient cyclization of ortho‐alkynylanilides. Among them, the reaction of ortho‐alkynylanilides (0.25 mmol) with iron(III) chloride (3.0 equiv.) and diorganyl diselenides (0.75 equiv.) in dichloromethane as solvent gave the products in acceptable to good yields. The resulting products were then subjected to a nitrogen–oxygen exchange reaction with ammonium acetate to furnish quinazoline derivatives. The one‐pot version of this cyclization, starting directly from 2‐alkynylanilines, avoiding the previous preparation of ortho‐alkynylanilides was also briefly studied.magnified image

  DOI：

  10.1002/adsc.201300925