甲氟磷 | 115-26-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 甲氟磷
• 中文别名: 氟化四甲基磷二酰胺；四甲氟；双(二甲胺基)磷酰氟；甲氯磷；氟甲胺磷
• 英文名称: dimefox
• 英文别名: Pestox XIV；bis(dimethylamino)phosphoro fluoridate；bis(dimethylamino)phosphoryl fluoride；tetramethyl-diamidophosphoryl fluoride；Phosphorsaeure-bis-dimethylamid-fluorid；Tetramethyl-diamidophosphorylfluorid；N-[dimethylamino(fluoro)phosphoryl]-N-methylmethanamine
• CAS: 115-26-4
• 化学式: C₄H₁₂FN₂OP
• 分子量: 154.124
• InChiKey: PGJBQBDNXAZHBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

血浆和组织酶负责将有机磷化合物水解成相应的磷酸和磷onic酸。然而，氧化酶也参与一些有机磷化合物的代谢。抗胆碱酯酶剂

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric and phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

代谢

有机磷抗胆碱酯酶剂在体内被一组称为A-酯酶或对氧磷酶的酶水解。这些酶存在于血浆和肝脏中，能够水解大量的有机磷化合物...通过断裂磷酯键、酐键、P-F键或P-CN键。/抗胆碱酯酶剂/

The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paraoxonases. These enzymes are found in the plasma and liver and hydrolyze a large number of organophosphorus compounds ... by cleaving the phosphoester, anhydride, P-F, or P-CN bonds. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒物 - 有机磷

Other Poison - Organophosphate

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

一些吩噻嗪类药物可能拮抗，而另一些可能增强有机磷杀虫剂的毒性抗胆碱酯酶效果。/有机磷胆碱酯酶抑制剂/

Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

巴比妥类药物可被抗胆碱酯酶增强。尽管巴比妥类药物可以谨慎用于治疗癫痫，但在处理由于抗胆碱酯酶导致的毒物中毒时，必须极度小心，特别是对于有机磷农药。毒扁豆碱是一种用作缩瞳剂的胆碱酯酶抑制剂，它增强其他类似抑制剂的效果...用于其他目的（叠加效应）或可能的协同作用。那些接触有机磷杀虫剂的人必须采取严格预防措施。...有机磷杀虫剂：叠加的抗胆碱酯酶效应。危险。使用抗胆碱酯酶的患者（即使是局部使用，如眼药水）应避免去最近使用过有机磷杀虫剂的地方。/抗胆碱酯酶/

Barbiturates are potentiated by anticholinesterases. Although barbiturates may be used cautiously in treating convulsions, extreme care is essential in handling poisonings due to anticholinesterases, particularly organophosphorus pesticides. Echothiophate, a cholinesterase inhibitor used as miotic, potentiates other such inhibitors ... used for other purposes (additive effects) or possibly synergistic. Those exposed to organophosphate insecticides must take strict precautions. ... Organophosphorus insecticides: additive anticholinesterase effects. Hazardous. Patients on Anticholinesterases (even topical, such as eye drops) should avoid areas where organophosphorus insecticides /have/ recently /been/ used. /Anticholinesterase/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

抗胆碱酯酶（有机磷）杀虫剂会对抗极化肌肉松弛剂。吩噻嗪类/和硫杂蒽类/：... 可能增强有机磷杀虫剂的有毒效果。/有机磷杀虫剂/

Anticholinesterase (organophosphorus) insecticides antagonize polarizing muscle relaxants. Phenothiazines /and thioxanthenes/: ... May enhance toxic effects of organophosphorus insecticides. /Organophosphorus insecticide/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

一个昏迷的病人，全身出汗，瞳孔缩小，衣物或呼吸中有杀虫剂的气味，并且肌肉出现颤动，这是有机磷中毒的典型表现。... 管理的具体步骤包括以下内容。1. 去污。... 2. 气道。如有必要，建立气道。... 3. 呼吸状态。事实上，这些病人由于多种原因经常出现呼吸窘迫。... 4. 心脏监测。... 5. 胆碱酯酶水平。... 6. 普瑞洛昔姆。普瑞洛昔姆是有机磷中毒的首选治疗方法，应几乎用于所有临床上有显著有机磷中毒的病人，特别是那些肌肉颤动和虚弱的病人。... 7. 阿托品。阿托品是有机磷中毒的生理性拮抗剂。当怀疑有机磷中毒时，应基于临床情况给予试验剂量的阿托品。/有机磷中毒/

A comatose patient who is diaphoretic, has pinpoint pupils and the odor of an insecticide on clothing or breath, and is noted to have muscle fasciculations represents the classic presentation of organophosphate poisoning. ... Specific steps in management include the following. 1. Decontamination. ... 2 Airway. Establish an airway if necessary. ... 3. Respiratory Status. Respiratory distress, in fact, is commonly found in these patients from multiple causes. ... 4. Cardiac Monitoring. ... 5. Cholinesterase Level. ... 6. Pralidoxime. Pralidoxime is the treatment of choice for organophosphate poisoning and should be used for nearly all patients with clinically significant orgnophosphate poisoning, particularly whose patients with muscular fasciculations and weakness. ... 7. Atropine. Atropine is the physiologic antidote for organophosphate poisoning. A trial dose of atropine should be instituted on clinical ground when one suspects organophosphate intoxication. /Organophosphate poisoning/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

经口给予大鼠后，药物通过尿液消除。

Following oral administration to rats, elimination is via the urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大多数有机磷化合物能够通过皮肤、结膜、胃肠道和肺部很好地吸收。/有机磷化合物/

Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷农药的皮肤吸收率可能会受到所使用溶剂的影响。

The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

许多有机磷杀虫剂会通过牛奶排出体外... /有机磷杀虫剂/

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  甲氟磷 在 fluorine-18 作用下， 以 水 、 乙腈 为溶剂， 生成 [18F]N,N,N',N'-tetramethylphosphorodiamidic fluoride
  参考文献：
  名称：

  用于水相容性 SN2 18F-氟化小分子放射性示踪剂的“AquaF”构建模块

  摘要：

  尽管广泛使用亲水结构单元来掺入18 F 并改善示踪剂药代动力学，但在水中实现有效的离去基团介导的亲核18 F-氟化（不包括18 F/ 19 F-交换）仍然是一个艰巨的挑战。在这里，我们提出了一种水相容的 S N 2 离去基团介导的18 F-氟化方法，该方法采用预共轭的“AquaF”（膦酰胺氟化物）构建块。在 19 个紧凑的四配位五价 P(V)–F 候选物中，“AquaF”结构单元表现出优异的水溶性、在水中足够的18 F-氟化能力以及优异的体内代谢特性。从候选离去基团池中鉴定出两个硝基吡啶醇离去基团，可进一步增强前体水溶性，能够在水中以 10 –2 M –1 s –1级反应速率常数进行18 F-氟化（超过18 F/ 19 F-交换）在室温下。随着放能协同 S N 2 18 F-氟化机制的确认，这种18 F-氟化方法实现了~90%的放射化学转化率，并在盐水中达到了 175 ± 40 GBq/μmol（使用

  DOI：

  10.1021/jacs.4c05854
• 作为产物：
  描述：

  八甲磷 在 potassium hydrogen bifluoride 、 苯 作用下， 生成 甲氟磷
  参考文献：
  名称：

  Schrader, 1947, # 714, p. 42

  摘要：

  DOI：
• 作为试剂：
  描述：

  四氢吡喃酮 、 4-methoxy-4-(3-mercaptophenyl)tetrahydropyran 、 1,3-二溴苯 、 碘甲烷 在 正丁基锂 、 sodium hydride 作用下， 以 甲氟磷 、 乙醇 、 正己烷 、 水 、 mineral oil 为溶剂， 生成 4-(3-bromophenyl)-4-methoxytetrahydro-2H-pyran
  参考文献：
  名称：

  Bicyclic pyran derivatives and their use as inhibitors of 5-lipoxygenase

  摘要：

  公开号：

  EP0462831B1

文献信息

• Fluorination of organochlorophosphorus compounds with alkali metal salts of perfluorinated complex anions. Part 2
  作者：Omar Farooq

  DOI：10.1039/a908932b

  日期：——

  Alkali metal salts of perfluorinated complex anions were used to fluorinate a few selected organochlorophosphorus compounds in the presence and absence of a multifunctional etheral solvent. Together with oxidative products, low to moderate yields of the desired monofluorinated products were obtained.

  在存在和不存在多功能醚溶剂的情况下，全氟化络合物阴离子的碱金属盐用于氟化一些选定的有机氯磷化合物。与氧化产物一起，获得所需产率的低至中等的单氟化产物。
• Rapid and efficient solid-supported reagent synthesis of fluorine derivatives of phosphorus(V) compounds
  作者：Timothy Sierakowski、James J. Kiddle

  DOI：10.1016/j.tetlet.2005.02.026

  日期：2005.3

  Direct conversion of phosphorus(V) chlorides to the corresponding phosphorus(V) fluorides was achieved utilizing a solid-supported reagent. The phosphorus(V) fluorides were straightforwardly synthesized and efficiently isolated in very good yields.

  利用固体负载的试剂可以将氯化磷（V）直接转化为相应的氟化磷（V）。氟（V）氟化物可以直接合成并以非常高的收率有效分离。
• Reactions of HMPA with hexafluorobenzene, pentafluorochlorobenzene and pentafluorophenol
  作者：Cheng-Pan Zhang、Qing-Yun Chen、Ji-Chang Xiao

  DOI：10.1016/j.jfluchem.2008.02.005

  日期：2008.5

  Hexamethylphophoramide (HMPA) reacted with hexafluorobenzene and its derivatives with good conversion to give dimethylaminated products and phosphorofluoridates, even in unfavorable reaction stoichiometries. An aromatic nucleophilic mechanism might be involved.

  六甲基磷酰胺（HMPA）与六氟苯及其衍生物反应，具有良好的转化率，即使在不利的化学计量比条件下，也能得到二甲基胺化的产物和氟代磷酸酯。可能涉及芳香亲核机制。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: P: MVol.C, 212, page 487 - 489
  作者：

  DOI：——

  日期：——
• Cook et al., Journal of the Chemical Society, 1949, p. 2921,2925
  作者：Cook et al.

  DOI：——

  日期：——