diethyl [1-(4-methoxyphenylamino)-but-2-enyl]-phosphonate | 131480-07-4

• 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-(4-methoxyphenylamino)-but-2-enyl]-phosphonate
• 英文别名: diethyl 1-(4-methoxyphenylamino)but-2-enephosphonate；N-[(E)-1-diethoxyphosphorylbut-2-enyl]-4-methoxyaniline
• CAS: 131480-07-4
• 化学式: C₁₅H₂₄NO₄P
• 分子量: 313.334
• InChiKey: PCOVCQZUAUIBKM-VMPITWQZSA-N

物化性质

• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl [1-(4-methoxyphenylamino)-but-2-enyl]-phosphonate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以62%的产率得到diethyl (1-amino-but-2-enyl)-phosphonate
  参考文献：
  名称：

  Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates

  摘要：

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.

  DOI：

  10.1021/jo062609+
• 作为产物：
  描述：

  1-叠氮基-4-甲氧基苯 、 diethyl (E)-but-2-enoylphosphonate 在 三甲基膦 、 dimethyl sulfide borane 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到diethyl [1-(4-methoxyphenylamino)-but-2-enyl]-phosphonate
  参考文献：
  名称：

  Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates

  摘要：

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.

  DOI：

  10.1021/jo062609+

文献信息

• Synthesis of organophosphorus compounds via silyl esters of phosphorous acids
  作者：Kamyar Afarinkia、Charles W. Rees、John I.G. Cadogan

  DOI：10.1016/s0040-4020(01)87899-6

  日期：1990.1

  The addition of trimethylsilyloxy phosphorus (III)derivatives generated in situ to imines at room temperature provides a mild selective and high yielding route to α-aminoalkylphosphorate and α-aminoalkylphenylphosphinate esters. Isocyanates and carbodiimides react similarly to give phosphonoureas and phosphonoguarnidines respectively aldehydes and ketones are much less reactive and cyanides are inert

  在室温下将原位产生的三甲基甲硅烷氧基磷（III）衍生物加到亚胺上，为α-氨基烷基磷酸酯和α-氨基烷基苯基次膦酸酯提供了温和的选择性和高产率的途径。异氰酸酯和碳二亚胺类似地反应，分别得到膦酰脲和膦酰胍，醛和酮的反应性低得多，氰化物是惰性的。
• Synthesis of α-Phosphorylated α,β-Unsaturated Imines and Their Selective Reduction to Vinylogous and Saturated α-Aminophosphonates
  作者：Francisco Palacios、Javier Vicario、Agnieszka Maliszewska、Domitila Aparicio

  DOI：10.1021/jo062609+

  日期：2007.3.1

  [GRAPHIC]An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.