diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-carbamoylphenyl)prop-1-enylphosphonate | 939387-74-3

• 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 (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-carbamoylphenyl)prop-1-enylphosphonate
• 英文别名: diethyl (Z)-3-(N-acetyl,N-(benzyloxy)amino)-1-(4-carbamoylphenyl)-propenylphosphonate；4-[(Z)-3-[acetyl(phenylmethoxy)amino]-1-diethoxyphosphorylprop-1-enyl]benzamide
• CAS: 939387-74-3
• 化学式: C₂₃H₂₉N₂O₆P
• 分子量: 460.467
• InChiKey: DBHBDVJZNCKRRD-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-carbamoylphenyl)prop-1-enylphosphonate 在 palladium on activated charcoal 三甲基溴硅烷 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 72.0h， 生成 3-[N-acetyl-N-(hydroxy)amino]-1-(4-carbamoylphenyl)propylphosphonate bisammonia salt
  参考文献：
  名称：

  Divergent Strategy for the Synthesis of α-Aryl-Substituted Fosmidomycin Analogues

  摘要：

  [GRAPHICS]Fosmidomycin is the first representative of a new class of antimalarial drugs acting through inhibition of 1-deoxy-D-xylulose 5-phosphate ( DOXP) reductoisomerase (DXR), an essential enzyme in the non-mevalonate pathway for the synthesis of isoprenoids. This work describes a divergent strategy for the synthesis of a series of alpha-aryl-substituted fosmidomycin analogues, featuring a palladium-catalyzed Stille coupling as the key step. An alpha-(4-cyanophenyl)fosmidomycin analogue emerged as the most potent analogue in the present series. Its antimalarial activity clearly surpasses that of the reference compound fosmidomycin.

  DOI：

  10.1021/jo0700981
• 作为产物：
  描述：

  diethyl (E)-3-[N-acetyl-N-(benzyloxy)amino]-1-(tributylstannyl)prop-1-enylphosphonate 、 4-碘苯甲酰胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex copper(l) iodide 、 三(2-呋喃基)膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以79%的产率得到diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(4-carbamoylphenyl)prop-1-enylphosphonate
  参考文献：
  名称：

  Divergent Strategy for the Synthesis of α-Aryl-Substituted Fosmidomycin Analogues

  摘要：

  [GRAPHICS]Fosmidomycin is the first representative of a new class of antimalarial drugs acting through inhibition of 1-deoxy-D-xylulose 5-phosphate ( DOXP) reductoisomerase (DXR), an essential enzyme in the non-mevalonate pathway for the synthesis of isoprenoids. This work describes a divergent strategy for the synthesis of a series of alpha-aryl-substituted fosmidomycin analogues, featuring a palladium-catalyzed Stille coupling as the key step. An alpha-(4-cyanophenyl)fosmidomycin analogue emerged as the most potent analogue in the present series. Its antimalarial activity clearly surpasses that of the reference compound fosmidomycin.

  DOI：

  10.1021/jo0700981