diethyl 1-(2'-furyl)-1-(diphenylmethylamino)methanephosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 1-(2'-furyl)-1-(diphenylmethylamino)methanephosphonate
• 英文别名: N-[diethoxyphosphoryl(furan-2-yl)methyl]-1,1-diphenylmethanamine
• 化学式: C₂₂H₂₆NO₄P
• 分子量: 399.426
• InChiKey: LIUCKUQCKDHXBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯甲胺盐酸盐 在 potassium carbonate 作用下， 反应 12.0h， 生成 diethyl 1-(2'-furyl)-1-(diphenylmethylamino)methanephosphonate
  参考文献：
  名称：

  1-AMINO-1-ARYL- AND 1-AMINO-1-HETEROARYL-METHANEPHOSPHONIC ACIDS AND THEIRN-BENZHYDRYL–PROTECTED DIETHYL ESTERS: PREPARATION AND CHARACTERIZATION

  摘要：

  N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1'-naphthyl, 9'-anthryl, T-pyrenyl) and 1-ainino-1-heteroaryl- (furyl, 2'-thienyl, X-thienyl, 2'-pyrrolyl)-methanephosphonic acids, prepared by the addition of diethyl phosphite to the corresponding benzhydryl imines, have been isolated, purified, and characterized. The presence of chiral alpha-carbon and prochiral phosphorus in these esters gives rise to complicated features in their NMR spectra, which are discussed. Hydrolysis of the crude 1-aryl compounds in situ gave modest yields of the corresponding aminophosphonic acids (except for 1'-pyrenyl). Of the 1-heteroaryl derivatives, only the 2'-thienyl compound gave the expected aminophosphonic acid; in other cases, alternative modes of decomposition may occur under hydrolytic conditions. NMR and mass spectral data are given for all products.

  DOI：

  10.1080/10426500490466274

文献信息

• Facile synthesis of α-amino phosphonates in water using a Lewis acid–surfactant-combined catalyst
  作者：Kei Manabe、Shū Kobayashi

  DOI：10.1039/b000319k

  日期：——

  Three-component reactions of aldehydes, amines and triethyl phosphite were efficiently catalyzed by scandium tris(dodecyl sulfate) at ambient temperature in water to give various α-amino phosphonates in high yields.

  三(十二烷基硫酸盐)钪在室温下在水中有效催化醛、胺和亚磷酸三乙酯的三组分反应，以高收率得到各种α-氨基膦酸酯。
• 1-AMINO-1-ARYL- AND 1-AMINO-1-HETEROARYL-METHANEPHOSPHONIC ACIDS AND THEIR<i>N</i>-BENZHYDRYL–PROTECTED DIETHYL ESTERS: PREPARATION AND CHARACTERIZATION
  作者：Harry R. Hudson、Rosalind J. Lee、Ray W. Matthews

  DOI：10.1080/10426500490466274

  日期：2004.9

  N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1'-naphthyl, 9'-anthryl, T-pyrenyl) and 1-ainino-1-heteroaryl- (furyl, 2'-thienyl, X-thienyl, 2'-pyrrolyl)-methanephosphonic acids, prepared by the addition of diethyl phosphite to the corresponding benzhydryl imines, have been isolated, purified, and characterized. The presence of chiral alpha-carbon and prochiral phosphorus in these esters gives rise to complicated features in their NMR spectra, which are discussed. Hydrolysis of the crude 1-aryl compounds in situ gave modest yields of the corresponding aminophosphonic acids (except for 1'-pyrenyl). Of the 1-heteroaryl derivatives, only the 2'-thienyl compound gave the expected aminophosphonic acid; in other cases, alternative modes of decomposition may occur under hydrolytic conditions. NMR and mass spectral data are given for all products.