(S)-(-)-O-ethyl S-methyl methylphosphonothioate | 51865-09-9

• 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
• 英文名称: (S)-(-)-O-ethyl S-methyl methylphosphonothioate
• 英文别名: S-(-) ethyl S-methyl methylphosphonothioate；(+)-(R)-Ethyl-S-methylmethylphosphonothioat；O-Ethyl S-methyl methylphosphonothiolate；1-[methyl(methylsulfanyl)phosphoryl]oxyethane
• CAS: 51865-09-9
• 化学式: C₄H₁₁O₂PS
• 分子量: 154.17
• InChiKey: RGYCUYGGOREOSJ-UHFFFAOYSA-N

物化性质

• 保留指数：
  1121;1121

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-O-ethyl S-methyl methylphosphonothioate 、 n-propylmagnesium iodide 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 methyl-n-propylphosphinic acid ethyl ester
  参考文献：
  名称：

  The reactions of ethoxy radicals with optically active tertiary phosphines. Stereochemistry of the substitution process and the question of permutation modes for the possible phosphoranyl radical intermediates

  摘要：

  DOI：

  10.1021/ja00357a016
• 作为产物：
  描述：

  Na salt of O-ethylmethylthiophosphonic acid 生成 (S)-(-)-O-ethyl S-methyl methylphosphonothioate
  参考文献：
  名称：

  Mastryukova,T.A. et al., Journal of general chemistry of the USSR, 1974, vol. 44, # 5, p. 963 - 971

  摘要：

  DOI：

文献信息

• Stereochemistry of some reactions between alkyl S-methyl methylphosphonothioates and chiral alkoxides
  作者：C. Richard Hall、Thomas D. Inch、Colin Pottage、Nancy E. Williams

  DOI：10.1016/s0040-4020(01)96731-6

  日期：1985.1

  te and (+)-pinacolyl alkoxide competitive and highly stereoselective displacements of O-alkyl and S-methyl occur, both reactions being with inversion of configuration. With the enantiomeric S-(-) ethyl (and methyl) S-methyl methylphosphonothioates and (+)-pinacolyl alkoxide the reactions, although still competitive, are no longer stereoselective. In contrast similar reactions with the sodium salt of

  在R-（+）乙基（或甲基）S-甲基甲基硫代磷酸酯和（+）-频哪醇烯醇盐的竞争下，发生O-烷基和S-甲基的立体选择性置换，这两个反应均与构型反转有关。用对映体S-（-）乙基（和甲基）S-甲基甲基硫代磷酸酯和（+）-频哪醇醇盐，反应尽管仍然具有竞争性，但不再是立体选择性的。相反，与（-）-薄荷醇钠盐的类似反应（可能被认为是（+）-频哪醇醇盐的镜像）在S-（-）上发生高度立体选择性，而在R-（+ ）对映体。当甲醇盐为亲核试剂时，未观察到乙醇，频哪醇醇盐和薄荷醇醇盐将烷基硫代甲基硫代磷酸烷基酯中的O-烷基取代。
• Convenient procedure for the stereospecific synthesis of optically active alkyl S-alkyl methylphosphonothioates, dialkyl S-alkyl phosphorothioates, dialkyl methylphosphonates, and trialkyl phosphates
  作者：David B. Cooper、C. Richard Hall、Thomas D. Inch

  DOI：10.1039/c39750000721

  日期：——

  Starting from the optically active cyclic esters prepared from ephedrine and RPSCl2(R = Cl or Me), optically active alkyl S-methyl methylphosphonothioates and dialkyl S-methyl phosphorothioates are isolated in yields of 32–60%, by a sequence which permits the assignment of absolute configuration to the products; bromine promoted methanolysis of the S–Me derivatives affords the corresponding O-methyl

  从麻黄碱和RPSCl 2（R = Cl或Me）制备的旋光性环状酯开始，分离旋光性烷基S-甲基甲基硫代磷酸酯和二烷基S-甲基硫代磷酸酯，其顺序允许为产品分配绝对配置；溴促进的S–Me衍生物的甲醇分解提供相应的O-甲基酯，其磷的构型反转。
• Hall, C. Richard; Inch, Thomas D.; Pottage, Colin, Journal of the Chemical Society. Perkin transactions I, 1983, p. 1967 - 1975
  作者：Hall, C. Richard、Inch, Thomas D.、Pottage, Colin、Williams, Nancy E.、Campbell, Malcolm M.、Kerr, Patrick F.

  DOI：——

  日期：——
• Optically active phosphines. Facile preparation of the optically active propylmethylbenzyl- and methylphenylbenzylphosphine oxides as precursors to the corresponding tertiary phosphines
  作者：Masaru Moriyama、Wesley G. Bentrude

  DOI：10.1021/ja00352a035

  日期：1983.7
• LeGras,P.G. et al., Journal of the Chemical Society. Perkin transactions II, 1973, p. 2064 - 2071
  作者：LeGras,P.G. et al.

  DOI：——

  日期：——

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