diethyl (1-fluorobut-3-en-1-yl)phosphonate

• 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 (1-fluorobut-3-en-1-yl)phosphonate
• 英文别名: diethyl 1-fluorobut-3-enylphosphonate；4-Diethoxyphosphoryl-4-fluorobut-1-ene
• 化学式: C₈H₁₆FO₃P
• 分子量: 210.185
• InChiKey: WZBBAIHSWNXWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1-fluorobut-3-en-1-yl)phosphonate 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.17h， 以44%的产率得到diethyl 1-fluoro-4-hydroxybutylphosphonate
  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：

  二乙基[二溴(氟)甲基]膦酸酯 在 正丁基锂 、 乙醇锂 作用下， 以 乙醇 为溶剂， 反应 0.84h， 生成 diethyl (1-fluorobut-3-en-1-yl)phosphonate
  参考文献：
  名称：

  Waschbuesch, Rachel; Carran, John; Savignac, Philippe, Journal of the Chemical Society. Perkin transactions I, 1997, # 8, p. 1135 - 1139

  摘要：

  DOI：

文献信息

• A new route to α-alkyl-α-fluoromethylenebisphosphonates
  作者：Petr Beier、Stanislav Opekar、Mikhail Zibinsky、Inessa Bychinskaya、G. K. Surya Prakash

  DOI：10.1039/c1ob05095h

  日期：——

  and alkyl halides using either caesium carbonate in DMF or sodium dimsyl. De-esterification of 2 provided biologically important α-alkyl-α-fluoromethylenebisphosphonic acid, 3, while alkoxide–induced carbon–phosphorus bond cleavage of 2 gave α-fluorophosphonates, 4, which are useful synthons in organic synthesis.

  从可商购的产品开始，已经开发出一种新的方法来生产α-烷基-α-氟亚甲基双膦酸酯2氟亚甲基双膦酸四乙酯（1），以及使用DMF中的碳酸铯或二甲基钠的烷基卤化物。的脱酯化2提供生物学上重要的α-烷基-α-fluoromethylenebisphosphonic酸，3，而醇盐诱导的碳-磷键裂解2，得到α-fluorophosphonates，4，这是有机合成中有用的合成子。
• A new route to α-fluoromethyl- and α-fluoroalkyl-phosphonates
  作者：Carl Patois、Philippe Savignac

  DOI：10.1039/c39930001711

  日期：——

  α-Fluoroalkylphosphonates are prepared by double-halogen exchange of 1,1,1-dibromofluoroalkylphosphonates with n-butyllithium–trimethylchlorosilane (2 : 1) followed by alkylation and ethanolysis.

  δ-氟烷基膦酸盐是通过 1,1,1-二溴氟烷基膦酸盐与正丁基锂三甲基氯硅烷（2:1）进行双卤素交换，然后进行烷基化和乙醇分解制备而成。
• The preparation of (EtO)2P(O)CFHZnBr and (EtO)2P(O)CFHCu and their utility in the preparation of functionalized α-fluorophosphonates
  作者：Xin Zhang、Weiming Qiu、Donald J. Burton

  DOI：10.1016/s0040-4039(99)00305-6

  日期：1999.4

  The organometallic reagent, (EtO)2P(O)CFHZnBr, was generated in situ in excellent yields via the reaction of (EtO)2P(O)CFHBr with zinc metal. Metathesis with Cu(I)Br gave (EtO)2P(O)CFHCu. The reagents exhibit excellent reactivity with substrates, such as allyl halides, alkynyl halides, vinyl halides, aryl halides and acyl or phosphoryl halides, and provide a useful one flask route to functionalized

  通过（EtO）2 P（O）CFHBr与锌金属的反应，原位生成有机金属试剂（EtO）2 P（O）CFHZnBr 。与Cu（I）Br复分解得到（EtO）2 P（O）CFHCu。该试剂与烯丙基卤，炔基卤，乙烯基卤，芳基卤和酰基或磷酰基卤等底物具有优异的反应性，并为官能化的α-氟代膦酸酯提供了一条有用的烧瓶法。
• 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.
• Waschbuesch, Rachel; Carran, John; Savignac, Philippe, Journal of the Chemical Society. Perkin transactions I, 1997, # 8, p. 1135 - 1139
  作者：Waschbuesch, Rachel、Carran, John、Savignac, Philippe

  DOI：——

  日期：——