O,O-diethylchloro-1 butenyl-3,4-phosphonate | 118512-73-5

• 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: O,O-diethylchloro-1 butenyl-3,4-phosphonate
• 英文别名: diethyl 1-chlorobut-3-enylphosphonate；4-Chloro-4-diethoxyphosphorylbut-1-ene
• CAS: 118512-73-5
• 化学式: C₈H₁₆ClO₃P
• 分子量: 226.64
• InChiKey: GTDYBAKLLGALLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  O,O-diethylchloro-1 butenyl-3,4-phosphonate 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 C₈H₁₈ClO₅P
  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：

  二甲基(氯甲基)丙烯酯 在 正丁基锂 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 2.25h， 生成 O,O-diethylchloro-1 butenyl-3,4-phosphonate
  参考文献：
  名称：

  Le O,O-diéthyltriméthylsilylchlorométhylphosphonate α-lithié (C2H5O)2P(O)C(Cl)Si(CH3)3Li

  摘要：

  DOI：

  10.1016/0022-328x(88)80003-2

文献信息

• Hydroboration of Unsaturated Phosphonic Esters:  Synthesis of Boronophosphonates and Trisubstituted Vinylphosphonates
  作者：Inna Pergament、Morris Srebnik

  DOI：10.1021/ol006836o

  日期：2001.1.1

  [figure: see text] Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates

  [图：见正文]用频哪醇硼烷（PBH）对膦酸乙烯基酯进行氢硼化可得到膦酰基硼酸酯2。令人惊讶的是，此类化合物以前尚未见报道。该反应与末端烯基膦酸酯一起很好地进行。内部链烯基膦酸酯产生复杂的混合物。单锅法将炔基膦酸酯与PBH进行硼氢化/铃木偶联，可得到具有良好总收率的三取代乙烯基膦酸酯，并提供了这些化合物的新合成方法。
• TEULADE, MARIE-PAULE;SAVIGNAC, PHILIPPE, J. ORGANOMET. CHEM., 338,(1988) N 3, 295-303
  作者：TEULADE, MARIE-PAULE、SAVIGNAC, PHILIPPE

  DOI：——

  日期：——
• Le O,O-diéthyltriméthylsilylchlorométhylphosphonate α-lithié (C2H5O)2P(O)C(Cl)Si(CH3)3Li
  作者：Marie-Paule Teulade、Philippe Savignac

  DOI：10.1016/0022-328x(88)80003-2

  日期：1988.1
• 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.