硫代磷酸O,O-二甲基S-(苯基甲基)酯 | 7205-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 硫代磷酸O,O-二甲基S-(苯基甲基)酯
• 英文名称: S-benzyl O,O-dimethyl phosphorothioate
• 英文别名: S-benzyl O,O-dimethyl phosphonothiolate；O,O-dimethyl S-(benzyl) phosphorothioate；O,O-dimethyl-S-benzyl thiophosphate；O,O-dimethyl-S-benzylphosphorothioat；thiophosphoric acid S-benzyl ester-O,O'-dimethyl ester；Thiophosphorsaeure-S-benzylester-O,O'-dimethylester；Dimethoxyphosphorylsulfanylmethylbenzene
• CAS: 7205-16-5
• 化学式: C₉H₁₃O₃PS
• 分子量: 232.24
• InChiKey: IIQZMUBPITYEIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三硫化苯甲基 、 三甲氧基磷 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 硫代磷酸O,O-二甲基S-(苯基甲基)酯
  参考文献：
  名称：

  Reaction of trialkyl phosphites with organic trisulfides. Synthetic and mechanistic aspects

  摘要：

  DOI：

  10.1021/jo01337a026

文献信息

• N-Chlorosuccinimide-promoted synthesis of thiophosphates from thiols and phosphonates under mild conditions
  作者：Yi-Chen Liu、Chin-Fa Lee

  DOI：10.1039/c3gc41839a

  日期：——

  A very simple N-chlorosuccinimide-promoted synthesis of thiophosphates through the coupling of thiols and phosphonates is reported. Notably, the reactions were carried out in the absence of a base. Functional groups including fluoro, bromo and trifluoromethyl are all tolerated by the reaction conditions employed. Both aryl and alkyl thiols are coupled smoothly with a broad spectrum of phosphonates to afford the corresponding thiophosphates in good to excellent yields.

  本文报道了一种通过巯基和膦酸酯的偶联反应，以N-氯代琥珀酰亚胺促进的硫代磷酸酯的简便合成方法。值得注意的是，这些反应是在无碱条件下进行的。所采用的反应条件能够容忍包括氟、溴和三氟甲基在内的多种官能团。无论是芳基还是烷基巯基，均能与一系列膦酸酯顺利偶联，从而以良好的至优异的产率得到相应的硫代磷酸酯。
• Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations
  作者：Szabolcs Kovács、Bilguun Bayarmagnai、Alexandre Aillerie、Lukas J. Gooßen

  DOI：10.1002/adsc.201701549

  日期：2018.5.16

  using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammonium O,O‐dimethyl phosphorothioate, was synthesized in near‐quantitative yield from Me3SiP(O)(OMe)2, elemental sulfur and Me4NF. Its umpolung with N‐bromophthalimide provided the electrophilic reagent, O,O‐dimethyl‐S‐(N‐phthalimido)phosphorothioate. Complementary methods based on these reagents enable the phosphorothiolation

  公开了新的晚期硫代磷酸化方法，该方法允许使用亲核试剂和亲电试剂将SP（O）（OR）2基团有效转移到功能不同的底物上。由Me 3 SiP（O）（OMe）2，元素硫和Me 4 NF以接近定量的产率合成了亲核试剂O，O-二甲基硫代磷酸四甲基铵。它与N-溴邻苯二甲酰亚胺一起提供亲电子试剂O，O-二甲基-S-（N‐phthalimido）硫代磷酸酯。基于这些试剂的补充方法可以在温和的条件下以良好的收率对各种功能化的卤代烷，芳族重氮盐，芳基硼酸和富电子芳烃进行硫代磷酸化。
• NHC‐Catalyzed Metathesis and Phosphorylation Reactions of Disulfides: Development and Mechanistic Insights
  作者：Reece D. Crocker、Mohanad A. Hussein、Junming Ho、Thanh V. Nguyen

  DOI：10.1002/chem.201700744

  日期：2017.5.5

  The development of efficient methods for the metathesis and phosphorylation reactions of disulfide compounds is of widespread interest due to their important synthetic utility in polymer, biological, medicinal and agricultural chemistry. Herein, we demonstrate the use of N‐heterocyclic carbenes (NHCs) as versatile organocatalysts to promote these challenging reactions under mild conditions. This metal‐

  由于二硫化物化合物在聚合物，生物，药物和农业化学中的重要合成用途，因此开发有效的二硫化合物的复分解和磷酸化反应方法的方法引起了广泛的兴趣。本文中，我们证明了使用N-杂环卡宾（NHC）作为通用有机催化剂在温和条件下促进这些具有挑战性的反应。这种不含金属和氧化剂的方案操作简单，反应时间非常短。NMR研究和高水平的从头算计算也阐明了这些反应中NHC的亲核性和碱性之间的相互作用。
• A new synthesis of thiophosphoric acid esters with a C-S-P bond
  作者：Christa E. Müller、Hermann J. Roth

  DOI：10.1016/0040-4039(90)87018-u

  日期：1990.1

  S-substituted thiosuccinimides 1a-d and thiophthalimides 2a-d were found to react with trialkylphosphites according to a Michaelis-Arbuzov type mechanism. This provides an efficient way to prepare thiophosphoric acid esters, particularly thiophospholipids, with a C-S-P bond.

  各种S-取代thiosuccinimides 1A-d和thiophthalimides图2a-d中发现根据一个的Michaelis-阿尔布佐夫型机构与三烷基亚反应。这提供了制备具有CSP键的硫代磷酸酯，特别是硫代磷脂的有效方法。
• Synthesis of Thiophosphates by Coupling of Phosphates with Bunte Salts under Mild Conditions
  作者：Sen Lin、Zhaohua Yan、Cong Min、Rongxing Zhang、Qian Liu

  DOI：10.1055/s-0037-1609556

  日期：2018.9

  A simple, green, and efficient method has been developed for the preparation of thiophosphates with sodium S-benzyl thiosulfates. The method uses an NaBr-catalyzed coupling reaction of Bunte salts with phosphonates in the presence of an acid and hydrogen peroxide (30%), and the desired products were obtained in good yields.

  开发了一种简单、绿色、高效的方法，用于用 S-苄基硫代硫酸钠制备硫代磷酸盐。该方法在酸和过氧化氢 (30%) 的存在下使用 NaBr 催化的 Bunte 盐与膦酸盐的偶联反应，并以良好的收率获得了所需的产物。