N,N'-dibenzyl-N,N'-dimethyl-P-(4-methoxyphenyl)phosphonic diamide | 1056473-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N'-dibenzyl-N,N'-dimethyl-P-(4-methoxyphenyl)phosphonic diamide
• 英文别名: N-[[benzyl(methyl)amino]-(4-methoxyphenyl)-oxidophosphaniumyl]-N-methyl-1-phenylmethanamine
• CAS: 1056473-75-6
• 化学式: C₂₃H₂₇N₂O₂P
• 分子量: 394.453
• InChiKey: JLJJMZNDMNRIPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-dibenzyl-N,N'-dimethyl-P-(4-methoxyphenyl)phosphonic diamide 在 N,N-二甲基丙烯基脲 、 仲丁基锂 、 甲醇 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.5h， 以60%的产率得到(1RS,3SR,3aSR,7aSR)-N-benzyl-3-phenyl-N,2-dimethyl-5-methoxy-2,3,3a,7a-tetrahydro-1H-2,1-benzazaphosphol-1-amine 1-oxide
  参考文献：
  名称：

  Dearomatizing Anionic Cyclization of Phosphonamides. A Route to Phosphonic Acid Derivatives with Antitumor Properties

  摘要：

  Deprotonation of bis(N-benzyl-N-methyl)-P-arylphosphonic diamides with s-BuLi in THF at -90 degrees C takes place selectively at the benzylic position. The anions undergo intramolecular attack to the P-aryl ring leading to dearomatized species that were trapped with a series of electrophiles (MeOH, ArOH, BnBr, aliphatic and aromatic aldehydes, and benzophenone) in very high yield, and with high regio- and stereocontrol. The dearomatized products were smoothly transformed into gamma-aminophosphonic acids under acidic conditions. Preliminary screening for antitumor activity showed promising levels of activity.

  DOI：

  10.1021/ol801463g
• 作为产物：
  描述：

  (4-甲氧基苯基)亚膦酸二氯化物 、 N-甲基苄胺 在 三乙胺 、 双氧水 作用下， 以 甲苯 、 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 N,N'-dibenzyl-N,N'-dimethyl-P-(4-methoxyphenyl)phosphonic diamide
  参考文献：
  名称：

  Dearomatizing Anionic Cyclization of Phosphonamides. A Route to Phosphonic Acid Derivatives with Antitumor Properties

  摘要：

  Deprotonation of bis(N-benzyl-N-methyl)-P-arylphosphonic diamides with s-BuLi in THF at -90 degrees C takes place selectively at the benzylic position. The anions undergo intramolecular attack to the P-aryl ring leading to dearomatized species that were trapped with a series of electrophiles (MeOH, ArOH, BnBr, aliphatic and aromatic aldehydes, and benzophenone) in very high yield, and with high regio- and stereocontrol. The dearomatized products were smoothly transformed into gamma-aminophosphonic acids under acidic conditions. Preliminary screening for antitumor activity showed promising levels of activity.

  DOI：

  10.1021/ol801463g