4-Diethoxyphosphoryl-4-fluorobutanoic acid | 1235988-34-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-Diethoxyphosphoryl-4-fluorobutanoic acid
• CAS: 1235988-34-7
• 化学式: C₈H₁₆FO₅P
• 分子量: 242.184
• InChiKey: ODKRRDZFQITYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Diethoxyphosphoryl-4-fluorobutanoic acid 、 N-methyl-O-benzylhydroxylamine trifluoroacetate 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以498 mg的产率得到diethyl 3-(N-(benzyloxy)-N-methylcarbamoyl)-1-fluoropropylphosphonate
  参考文献：
  名称：

  Synthesis and Evaluation of α-Halogenated Analogues of 3-(Acetylhydroxyamino)propylphosphonic Acid (FR900098) as Antimalarials

  摘要：

  Three alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) have been synthesized from diethyl but-3-enylphosphonate using a previously described method for the alpha-halogenation of alkylphosphonates. These analogues were evaluated for antimalarial potential in vitro against Plasmodium falciparum and in vivo in the P. berghei mouse model. All three analogues showed higher in vitro and/or in vivo potency than the reference compounds.

  DOI：

  10.1021/jm100211e
• 作为产物：
  描述：

  diethyl 1-fluoro-4-hydroxybutylphosphonate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 水 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以100%的产率得到4-Diethoxyphosphoryl-4-fluorobutanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of α-Halogenated Analogues of 3-(Acetylhydroxyamino)propylphosphonic Acid (FR900098) as Antimalarials

  摘要：

  Three alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) have been synthesized from diethyl but-3-enylphosphonate using a previously described method for the alpha-halogenation of alkylphosphonates. These analogues were evaluated for antimalarial potential in vitro against Plasmodium falciparum and in vivo in the P. berghei mouse model. All three analogues showed higher in vitro and/or in vivo potency than the reference compounds.

  DOI：

  10.1021/jm100211e

文献信息

• Synthesis and Evaluation of α-Halogenated Analogues of 3-(Acetylhydroxyamino)propylphosphonic Acid (FR900098) as Antimalarials
  作者：Thomas Verbrugghen、Paul Cos、Louis Maes、Serge Van Calenbergh

  DOI：10.1021/jm100211e

  日期：2010.7.22

  Three alpha-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) have been synthesized from diethyl but-3-enylphosphonate using a previously described method for the alpha-halogenation of alkylphosphonates. These analogues were evaluated for antimalarial potential in vitro against Plasmodium falciparum and in vivo in the P. berghei mouse model. All three analogues showed higher in vitro and/or in vivo potency than the reference compounds.