diethyl (3,5-dibromo-4-hydroxyphenylamino)(4-methoxyphenyl)methylphosphonate | 1522415-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (3,5-dibromo-4-hydroxyphenylamino)(4-methoxyphenyl)methylphosphonate
• 英文别名: 2,6-Dibromo-4-[[diethoxyphosphoryl-(4-methoxyphenyl)methyl]amino]phenol；2,6-dibromo-4-[[diethoxyphosphoryl-(4-methoxyphenyl)methyl]amino]phenol
• CAS: 1522415-27-5
• 化学式: C₁₈H₂₂Br₂NO₅P
• 分子量: 523.158
• InChiKey: SCWMSVLZQKBTQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基-2,6-二溴苯酚 、 4-甲氧基苯甲醛 、 亚磷酸二乙酯 在 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 0.18h， 以90%的产率得到diethyl (3,5-dibromo-4-hydroxyphenylamino)(4-methoxyphenyl)methylphosphonate
  参考文献：
  名称：

  CeCl₃·7H₂O Catalyzed, Microwave-Assisted High-Yield Synthesis of α-Aminophosphonates and their Biological Studies

  摘要：

  A new class of diethyl(3,5-dibromo-4-hydroxyphenylamino) (substituted phenyl/heterocyclic) methylphosphonates 4(a-j) has been synthesized by one-pot three component simultaneous reaction (Kabachnik-Fields) of 4-amino-2,6-dibromophenol 1, substituted heterocyclic/phenyl aldehydes 2(a-j), and diethylphosphite 3 using a Lewis acid catalyst, CeCl(3)7H(2)O (5mol%) under microwave irradiation as well as conventional conditions. It was observed that microwave irradiation method is more facile, efficient, and advantageous with respect to reaction time and yields. The structures of all the synthesized compounds were supported by analyzing IR, H-1/C-13/P-31 NMR, and mass spectral data. The synthesized compounds were screened for their in vitro antimicrobial and antioxidant activities.

  DOI：

  10.1080/10426507.2013.798785

文献信息

• CeCl₃·7H₂O Catalyzed, Microwave-Assisted High-Yield Synthesis of α-Aminophosphonates and their Biological Studies
  作者：M. Varalakshmi、D. Srinivasulu、D. Rajasekhar、C. Naga Raju、S. Sreevani

  DOI：10.1080/10426507.2013.798785

  日期：2014.1

  A new class of diethyl(3,5-dibromo-4-hydroxyphenylamino) (substituted phenyl/heterocyclic) methylphosphonates 4(a-j) has been synthesized by one-pot three component simultaneous reaction (Kabachnik-Fields) of 4-amino-2,6-dibromophenol 1, substituted heterocyclic/phenyl aldehydes 2(a-j), and diethylphosphite 3 using a Lewis acid catalyst, CeCl(3)7H(2)O (5mol%) under microwave irradiation as well as conventional conditions. It was observed that microwave irradiation method is more facile, efficient, and advantageous with respect to reaction time and yields. The structures of all the synthesized compounds were supported by analyzing IR, H-1/C-13/P-31 NMR, and mass spectral data. The synthesized compounds were screened for their in vitro antimicrobial and antioxidant activities.