ethyl ethylphosphonofluoridate | 650-20-4

• 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: ethyl ethylphosphonofluoridate
• 英文别名: Ethylphosphonsaeure-ethylester-fluorid；Ethyl-ethylphosphonofluoridat；Ethylethylfluorophosphonat；1-[ethyl(fluoro)phosphoryl]oxyethane
• CAS: 650-20-4
• 化学式: C₄H₁₀FO₂P
• 分子量: 140.094
• InChiKey: RORQVZRCLFKMMP-UHFFFAOYSA-N

物化性质

• 保留指数：
  866;866;865.7

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl ethylphosphonofluoridate 在 四氯苯基-膦烷 作用下， 生成 1-[氯(氟)磷酰基]乙烷
  参考文献：
  名称：

  Kozhushko, B. N.; Paliichuk, Yu. A.; Bogel'fer, L. Ya., Journal of general chemistry of the USSR, 1980, vol. 50, # 6, p. 1029 - 1041

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl ethylphosphonochloridate 在 TBAF(tBuOH)4 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以93%的产率得到ethyl ethylphosphonofluoridate
  参考文献：
  名称：

  四（叔丁醇）四丁基铵配位氟化物-一种合成磷（V）化合物氟衍生物的有效试剂

  摘要：

  使用固体试剂四（叔丁醇）配位的四丁基铵可实现氯化磷（V）直接转化为相应的氟化磷（V）。直接合成了氟（V）氟化物，并以非常高的收率有效地进行了分离。

  DOI：

  10.1016/j.tetlet.2009.03.151

文献信息

• Kinetics of reactions of ethylp-nitrophenyl ethylphosphonate with anionic nucleophiles in a detergentless microemulsion
  作者：V. E. Bel'skii、F. G. Valeeva

  DOI：10.1007/bf02498265

  日期：1999.12

  The kinetics of reactions of ethylp-nitrophenyl ethylphosphonate with anionic nucleophiles in a detergentless water—oil microemulsion, formed in then-hexane—water—isopropyl alcohol system, was studied. The rate constants of the reactions in the microemulsion are higher than those in aqueous solutions and increase with increasing isopropyl alcohol: water ratio.

  研究了乙基对硝基苯基乙基膦酸酯与阴离子亲核试剂在无洗涤剂水-油微乳液中的反应动力学，然后在己烷-水-异丙醇体系中形成。微乳液中的反应速率常数高于水溶液中的反应速率常数，并且随着异丙醇：水比的增加而增加。
• Ethyl Octylphosphonofluoridate and Analogs: Optimized Inhibitors of Neuropathy Target Esterase
  作者：Shao-Yong Wu、John E. Casida

  DOI：10.1021/tx00050a011

  日期：1995.12

  The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The principal compounds studied are alkyl alkylphosphonofluoridates and dialkyl phosphorofluoridates. Potencies that exceed those of any previous inhibitors under the standard in vitro NTE assay condition are achieved with alkyl octylphosphonofluoridates (ethyl, isopropyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, and 3-iodopropyl), 2-iodoethyl hexylphosphonofluoridate, and dialkyl phosphorofluoridates [ethyl, nonyl; di(2-iodoethyl); di(3-iodopropyl); dipentyl]. The concentration for 50% NTE inhibition (I-50) Of these compounds is 0.04-0.14 nM. Thirty-eight less active analogs including aryl phosphonates and aryl phosphates give I(50)s of 0.27-4730 nM. For highest potency the summation of length of the alkyl and alkoxy groups on phosphorus should be 12-16 atoms (carbons, oxygens, and phosphorus) (a terminal iodo substituent in this relationship is equivalent to a propyl group). In general, the phosphonofluoridates and phosphorofluoridates are more active than analogs with leaving groups other than fluorine, i.e., phenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 3,4-dichlorophenoxy, and 4H-1,3,2-benzodioxaphosphorin. Considering the exceptional potencies of ethyl and 2-iodoethyl octylphosphonofluoridates (I50S of 0.04 and 0.09 nM, respectively), it is not surprising that at ip doses of 10-30 mg/kg they inhibit brain NTE by 82-97% 48 h after treatment. However, unexpectedly, only the ethyl but not the 2-iodoethyl compound induces OPIDN, possibly associated with the greater ease of aging for NTE inhibited with the ethyl than the 2-iodoethyl compound (as observed in vitro both spontaneously and on induction by potassium fluoride). The high potency of ethyl octylphosphonofluoridate and several analogs as NTE inhibitors suggests that they are useful probes in determining the toxicological features of this secondary lesion for organophosphorus poisoning.
• ——
  作者：Simanenko、Popov、Prokop'eva、Karpichev、Savelova、Suprun、Bunton

  DOI：10.1023/a:1021699628721

  日期：——
• Yakubovich,A.Ya. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 1405 - 1406
  作者：Yakubovich,A.Ya. et al.

  DOI：——

  日期：——
• Drozd,G.I. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 558 - 562
  作者：Drozd,G.I. et al.

  DOI：——

  日期：——

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