1-benzyl-3-diethoxyphosphoryloxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone | 1615652-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-benzyl-3-diethoxyphosphoryloxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone
• 英文别名: 1-Benzyl-3-[diethoxy(oxido)phosphaniumyl]oxy-4-methylidene-3-phenylquinolin-2-one；1-benzyl-3-[diethoxy(oxido)phosphaniumyl]oxy-4-methylidene-3-phenylquinolin-2-one
• CAS: 1615652-89-5
• 化学式: C₂₇H₂₈NO₅P
• 分子量: 477.497
• InChiKey: WINDIGHQWODKSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-diethoxyphosphoryloxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到1-benzyl-3-hydroxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone
  参考文献：
  名称：

  Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base

  摘要：

  A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.

  DOI：

  10.1021/ol501479t
• 作为产物：
  描述：

  苄基(2-乙炔基苯基)胺 在 1,1-二氯甲醚 、 1-叔丁基-2,2,4,4,4-五(二甲氨基)-2Λ5,4Λ5-连二(磷氮基化合物) 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 29.0h， 生成 1-benzyl-3-diethoxyphosphoryloxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone
  参考文献：
  名称：

  Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base

  摘要：

  A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.

  DOI：

  10.1021/ol501479t

文献信息

• Intramolecular Cyclization of Alkynyl α-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base
  作者：Azusa Kondoh、Takuma Aoki、Masahiro Terada

  DOI：10.1021/ol501479t

  日期：2014.7.3

  A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.