甲氧基(甲基硫烷基)次膦酸 | 42576-53-4

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机硫代磷化合物
• 中文名称: 甲氧基(甲基硫烷基)次膦酸
• 英文名称: O,S-dimethyl phosphorothiolate
• 英文别名: thiophosphoric acid O,S-dimethyl ester；Thiophosphorsaeure-O,S-dimethylester；O,S-Dimethyl-hydrogenthiophosphat；O.S-Dimethyl-thiophosphat；Thiophosphorsaeure-O,S-dimethylester；O,S-Dimethyl-thiophosphorsaeure；Phosphorothioic acid, O,S-dimethyl ester；methoxy(methylsulfanyl)phosphinic acid
• CAS: 42576-53-4
• 化学式: C₂H₇O₃PS
• 分子量: 142.116
• InChiKey: UBRYVVDAYNKOOR-UHFFFAOYSA-N

物化性质

• 沸点：
  222.8±23.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2920190090

反应信息

• 作为反应物：
  描述：

  甲氧基(甲基硫烷基)次膦酸 在 potassium tetraiodomercurate(II) 、 水 作用下， 生成 trimethyl sulfonium ; tetraiodomercurate(II)
  参考文献：
  名称：

  Hilgetag et al., Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4>9, p. 73,75,86

  摘要：

  DOI：
• 作为产物：
  描述：

  O,O,O-三甲基巯基磷酸酯 在 丙酮 、 sodium iodide 作用下， 生成 甲氧基(甲基硫烷基)次膦酸
  参考文献：
  名称：

  Hilgetag; Teichmann, Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4>8, p. 97,101

  摘要：

  DOI：

文献信息

• <i>S</i>-Methylation of <i>O,O-</i>Dialkyl Phosphorodithioic Acids:  <i>O,O,S</i>-Trimethyl Phosphorodithioate and Phosphorothiolate as Metabolites of Dimethoate in Mice
  作者：Mahmoud Mahajna、Gary B. Quistad、John E. Casida

  DOI：10.1021/tx9600715

  日期：1996.1.1

  MeO(HS)P(O)SMe, MeO(HO)P(O)SMe, (MeO)2P(S)SMe, and (MeO)2P-(O)SMe; the latter two compounds are also established by GC-MS as dimethoate metabolites in mouse urine, liver, kidney, and lung. Several approaches verified unequivocally that the previously unknown P-SMe metabolites in urine and tissues are due to in vivo S-methylation rather than to impurities. Studies with other O,O-dimethyl and O,O-diethyl

  O，O，S-三甲基二硫代磷酸酯和硫代磷酸酯[（MeO）2P（S）SMe和（MeO）2P-（O）SMe分别是一些主要O中的杂质，延迟毒物和脱毒抑制剂，O-二甲基二硫代磷酸酯杀虫剂。我们最近的研究表明，小鼠中一硫代氨基甲酸和二硫代氨基甲酸具有广泛的S-甲基化，这表明诸如（MeO）2P（S）SH的二硫代磷酸也可能会进行S-甲基化。在腹腔镜治疗的小鼠中检查了这种可能性，重点研究了乐果[[MeO）2P（S）SCH2C（O）NHMe]的代谢产物，这是最重要的有机磷杀虫剂之一。乐果的尿代谢产物不含P-SMe取代基，经发现包含31种NMR光谱法鉴定为MeO（HS）P（O）SMe，MeO（HO）P（O）SMe的四种具有P-SMe部分的化合物，（MeO）2P（S）SMe和（MeO）2P-（O）SMe; 后两种化合物也通过GC-MS建立为乐果在小鼠尿液，肝，肾和肺中的代谢物。几种方法明确地证实，尿液和组织中以前
• Oxidative Bioactivation of Methamidophos Insecticide:  Synthesis of <i>N</i>-Hydroxymethamidophos (A Candidate Metabolite) and Its Proposed Alternative Reactions Involving N → O Rearrangement or Fragmentation through a Metaphosphate Analogue
  作者：Mahmoud Mahajna、John E. Casida

  DOI：10.1021/tx9701135

  日期：1998.1.1

  The systemic insecticide methamidophos, MeO(MeS)P(O)NH2, is a very weak inhibitor of acetylcholinesterase (AChE) in vitro relative to in vivo suggesting bioactivation. This hypothesis is supported by finding that brain AChE inhibition and poisoning signs from methamidophos are greatly delayed in mice and houseflies pretreated with oxidase inhibitors in an order for effectiveness of methimazole > N-benzylimidazole >> piperonyl butoxide. In contrast, the order for delaying parathion-induced AChE inhibition and toxicity is N-benzylimidazole >> piperonyl butoxide or methimazole, suggesting that different oxidases are involved in methamidophos and parathion activation. N-Hydroxylation is examined here as an alternative to the controversial S-oxidation proposed earlier for methamidophos activation. N-Hydroxymethamidophos [MeO(MeS)P(O)NHOH], synthesized by coupling MeO(MeS)P(O)Cl and Me-3-SiNHOSiMe3 followed by desilylation, is unstable at pH 7.4 (t(1/2) = 10 min at 37 degrees C) with decomposition by two distinct and novel mechanisms. The first mechanism (A) is N --> O rearrangement to MeO(MeS)P(O)ONH2 and then hydrolysis to MeO(MeS)P(O)OH, a sequence also established in the analogous series of (MeO)(2)P(O)NHOH --> (MeO)(2)P(O)ONH2 --> (MeO)(2)P(O)OH. The second mechanism (B) is proposed to involve tautomerism to the phosphimino form [MeO(MeS)P(OH)=NOH] that eliminates MeSH forming a metaphosphate analogue [MeOP(O)=NOH] trapped by water to give MeO(HO)P(O)NHOH that undergoes the N --> O rearrangement as above and hydrolysis to MeOP(O)(OH)(2). As a metaphosphate analogue, the metaphosphorimidate generated from MeO(MeS)P(O)NHOH in aqueous ethanol yields MeOP(O)(OH)(2) and MeO(EtO)P(O)OH in the same ratio as the solvents on a molar basis. Reactions of the N- and O-methyl derivatives of MeO(MeS)P(O)NHOH and (MeO)(2)P(O)NHOH are consistent with proposed mechanisms A and B. N-Hydroxymethamidophos is less potent than methamidophos as an AChE inhibitor and toxicant possibly associated with its rapid hydrolysis. Bioactivation of methamidophos via a metaphosphate analogue would directly yield a phosphorylated and aged AChE resistant to reactivating agents, an intriguing hypothesis worthy of further consideration.
• Hilgetag; Teichmann, Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4>8, p. 97,101
  作者：Hilgetag、Teichmann

  DOI：——

  日期：——
• Hilgetag et al., Journal fur praktische Chemie (Leipzig 1954), 1959, vol. <4>9, p. 73,75,86
  作者：Hilgetag et al.

  DOI：——

  日期：——