去甲基-甲基对硫磷 | 7699-30-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 中文名称: 去甲基-甲基对硫磷
• 中文别名: 纤维素,2-硫代乙基醚
• 英文名称: methyl p-nitrophenyl phosphorothioic acid
• 英文别名: opt.-active !-thiophosphoric acid O-methyl ester-O'-(4-nitro-phenyl ester)；opt.-akt.-Thiophosphorsaeure-O-methylester-O'-(4-nitro-phenylester)；(+/-)-Thiophosphorsaeure-O-methylester-O'-(4-nitro-phenylester)；1-(Methoxy-oxido-sulfanylphosphaniumyl)oxy-4-nitrobenzene；1-(methoxy-oxido-sulfanylphosphaniumyl)oxy-4-nitrobenzene
• CAS: 7699-30-1
• 化学式: C₇H₈NO₅PS
• 分子量: 249.184
• InChiKey: UEMHPBBZLQPEBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  去甲基-甲基对硫磷 在 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以90%的产率得到methyl p-nitrophenyl phosphorochloridothionate
  参考文献：
  名称：

  的两种对映体的立体选择性合成P -chirogenic 2-氧代-2-硫代-1,3,2- oxazaphosphorinane四甲基铵盐作为关键前体在结构上不同的手性衍生物

  摘要：

  2-氧代-2-硫代-1,3,2- oxazaphosphorinanyl盐的两种对映体的完全立体选择性合成已在五个步骤而完成的具有总体40-45％的产率从非对映异构起始Ñ甲基-methylstrychninium盐p -硝基苯基硫代磷酸。将其转化为对氯苯基硫代氯代磷酸对硝基苯基酯的两步磷酸化剂的对映体形式，可以在该反应序列中形成1,3,2-氧杂氮杂正膦环。开发了对映纯标题盐的另一种四步方法，该方法涉及第一步和关键步骤是硫代磷酰氯与N之间的环缩合含有1，3-氨基丙醇基的-α-萘乙基几乎完全具有非对映选择性。

  DOI：

  10.1016/j.tet.2011.10.085
• 作为产物：
  描述：

  甲基对硫磷 在 二乙胺 作用下， 以 乙醚 为溶剂， 生成 去甲基-甲基对硫磷
  参考文献：
  名称：

  Mel'nikov,N.N. et al., Journal of general chemistry of the USSR, 1961, vol. 31, # 11, p. 3361 - 3365

  摘要：

  DOI：

文献信息

• Divalent Metal Ion-Catalyzed Hydrolysis of Phosphorothionate Ester Pesticides and Their Corresponding Oxonates
  作者：Jean M. Smolen、Alan T. Stone

  DOI：10.1021/es960499q

  日期：1997.6.1

  The divalent metal ion-catalyzed hydrolysis of thionate (P=S) and oxonate (P=O) organophosphorus pesticides has been examined in light of three possible catalysis mechanisms: (1) metal ion coordination of the thionate sulfur or oxonate oxygen to enhance the electrophilicity of the phosphorus electrophilic site; (2) metal ion coordination and induced deprotonation of water to create a reactive nucleophile; and (3) metal ion coordination of the leaving group to facilitate its exit. The effect of the following metals at a concentration of 1 mM was examined: COII, Ni-II, Cu-II, Zn-II and Pb-II. These metal ions were chosen for their ability to complex organic ligands and inorganic nucleophiles. Of these metal ions, Cu-II possesses properties most suitable for all three catalytic mechanisms and serves as the most effective catalyst for the five thionate esters (chlorpyrifos-methyl, zinophos, diazinon, parathion-methyi, and ronnel) and the two oxonate esters (chlorpyrifos-methyl oxon and paraoxon) included in this study. A decrease in the degree of Cu-II catalysis at high pH arises from solubility limitations. Pb-II nearly matches Cu-II as a catalyst for oxonate esters, but is a less effective catalyst for thionate esters. Catalysis by Co-II, Ni-II, and Zn-II is negligible. Phenolate product analysis indicates that metal catalysis in some instances shifts hydrolysis from alkyl carbon-centered pathways to phosphorus-centered pathways.
• A chemical model for the enzymatic mono de-alkylation of (methyl and ethyl) parathion by glutathione-S-transferase
  作者：Marie Dolores Maturano、Véronique Bongibault、Michèle Willson、Alain Klaébé、Didier Fournier

  DOI：10.1016/s0040-4020(97)10176-4

  日期：1997.12
• BAKEEVA, R. F.;BELSKIJ, V. E.;KUDRYAVTSEVA, L. A.;DMITRIEVA, G. V.;IVANOV+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 1165-1167
  作者：BAKEEVA, R. F.、BELSKIJ, V. E.、KUDRYAVTSEVA, L. A.、DMITRIEVA, G. V.、IVANOV+

  DOI：——

  日期：——
• Stereoselective synthesis of both enantiomers of P-chirogenic 2-oxo-2-thio-1,3,2-oxazaphosphorinane tetramethylammonium salt as key precursors to structurally diverse chiral derivatives
  作者：Marian Mikołajczyk、Jerzy Łuczak、Lesław Sieroń、Michał W. Wieczorek

  DOI：10.1016/j.tet.2011.10.085

  日期：2012.1

  A fully stereoselective synthesis of both enantiomers of 2-oxo-2-thio-1,3,2-oxazaphosphorinanyl salt has been accomplished in five steps with an overall 40–45% yield starting from the diastereoisomeric N-methylstrychninium salts of methyl p-nitrophenyl phosphorothioic acid. Their conversion to the enantiomeric forms of methyl p-nitrophenyl phosphorochloridothionate as a two-step phosphorylating agent

  2-氧代-2-硫代-1,3,2- oxazaphosphorinanyl盐的两种对映体的完全立体选择性合成已在五个步骤而完成的具有总体40-45％的产率从非对映异构起始Ñ甲基-methylstrychninium盐p -硝基苯基硫代磷酸。将其转化为对氯苯基硫代氯代磷酸对硝基苯基酯的两步磷酸化剂的对映体形式，可以在该反应序列中形成1,3,2-氧杂氮杂正膦环。开发了对映纯标题盐的另一种四步方法，该方法涉及第一步和关键步骤是硫代磷酰氯与N之间的环缩合含有1，3-氨基丙醇基的-α-萘乙基几乎完全具有非对映选择性。
• Mel'nikov,N.N. et al., Journal of general chemistry of the USSR, 1961, vol. 31, # 11, p. 3361 - 3365
  作者：Mel'nikov,N.N. et al.

  DOI：——

  日期：——