diethyl (E)-[N-(hydroxy)imino](phenyl)methylphosphonate | 122203-27-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (E)-[N-(hydroxy)imino](phenyl)methylphosphonate
• 英文别名: (NE)-N-[diethoxyphosphoryl(phenyl)methylidene]hydroxylamine
• CAS: 122203-27-4
• 化学式: C₁₁H₁₆NO₄P
• 分子量: 257.226
• InChiKey: GQRDCKBYLSNMFP-VAWYXSNFSA-N

物化性质

• 沸点：
  362.9±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (E)-[N-(hydroxy)imino](phenyl)methylphosphonate 在 sodium tetrahydroborate 、 molybdenum(VI) oxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以92%的产率得到diethyl 1-aminophenylmethylphosphonate
  参考文献：
  名称：

  A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

  摘要：

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.

  DOI：

  10.1016/0040-4039(95)02171-x
• 作为产物：
  描述：

  苯甲酰膦酸二乙酯 在 盐酸羟胺 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 diethyl (E)-[N-(hydroxy)imino](phenyl)methylphosphonate
  参考文献：
  名称：

  A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

  摘要：

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.

  DOI：

  10.1016/0040-4039(95)02171-x

文献信息

• Palladium-Catalyzed Asymmetric Hydrogenation of<i>N</i>-Hydroxy-α-imino Phosphonates Using Brønsted Acid as Activator: The First Catalytic Enantioselective Approach to Chiral<i>N</i>-Hydroxy-α-amino Phosphonates
  作者：Nataliya S. Goulioukina、Ilya A. Shergold、Grigorii N. Bondarenko、Mikhail M. Ilyin、Vadim A. Davankov、Irina P. Beletskaya

  DOI：10.1002/adsc.201200170

  日期：2012.10.8

  The enantioselective synthesis of ring-substituted [N-(hydroxy)amino](phenyl)methylphosphonic esters via asymmetric hydrogenation of the corresponding N-hydroxy-α-imino phosphonates with up to 90% ee was developed using catalytic amounts of palladium(II) acetate and (R)-BINAP in 2,2,2-trifluoroethanol with a Brønsted acid as an activator.

  使用催化量的钯（II），通过不对称氢化相应的N-羟基-α-亚氨基膦酸酯（不超过90％ee），开发了环取代的[ N-（羟基）氨基]（苯基）甲基膦酸酯的对映选择性合成乙酸和（R）-BINAP在2,2,2-三氟乙醇中的溶液，以布朗斯台德酸为活化剂。
• Breuer,Eli; Karaman, Rafik; Goldblum, Amiram, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3047 - 3058
  作者：Breuer,Eli、Karaman, Rafik、Goldblum, Amiram、Gibson, Dan、Leader, Haim、et. al.

  DOI：——

  日期：——
• BREUER, ELI;KARAMAN, RAFIK;GOLDBLUM, AMIRAM;GIBSON, DAN;LEADER, HAIM;POTT+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N1, C. 3047-3057
  作者：BREUER, ELI、KARAMAN, RAFIK、GOLDBLUM, AMIRAM、GIBSON, DAN、LEADER, HAIM、POTT+

  DOI：——

  日期：——
• KRZYZANOWSKA, BOZENNA;PILICHOWSKA, SLAWOMIRA, POL. J. CHEM., 62,(1988) N-3, C. 165-177
  作者：KRZYZANOWSKA, BOZENNA、PILICHOWSKA, SLAWOMIRA

  DOI：——

  日期：——
• KAUSHIK, MAHABIR P.;VAIDYANATHASWAMY, RAMAMOORTHY, CHEM. AND IND.,(1989) N2, C. 389
  作者：KAUSHIK, MAHABIR P.、VAIDYANATHASWAMY, RAMAMOORTHY

  DOI：——

  日期：——