O,O-dimethyl S-phenyl phosphorothioate | 4237-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O,O-dimethyl S-phenyl phosphorothioate
• 英文别名: Dimethoxyphosphorylsulfanylbenzene
• CAS: 4237-00-7
• 化学式: C₈H₁₁O₃PS
• 分子量: 218.213
• InChiKey: RUHGOLPVRHFAJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 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：

  O,O-dimethyl S-phenyl phosphorothioate 在 1,3-dithia-2,4-diphosphetane-2,4-disulfides 作用下， 以 xylene 为溶剂， 反应 2.0h， 以92%的产率得到(dimethoxythiophosphinoylmercapto)benzene
  参考文献：
  名称：

  Yousif, N. M.; Gadalla, K. Z.; Yassin, S. M., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 60, # 3/4, p. 261 - 263

  摘要：

  DOI：
• 作为产物：
  描述：

  在 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 生成 O,O-dimethyl S-phenyl phosphorothioate
  参考文献：
  名称：

  Esters of tervalent phosphorus thio acids

  摘要：

  DOI：

  10.1007/bf00907045

文献信息

• Magnetically recyclable Cu-BTC@Fe₃O₄ composite-catalyzed C_(aryl)–S–P bond formation using aniline, P(O)H compounds and sulfur powder
  作者：Liang Wang、Sen Yang、Le Chen、Sheng Yuan、Qun Chen、Ming-Yang He、Zhi-Hui Zhang

  DOI：10.1039/c7cy00467b

  日期：——

  Cu-BTC@Fe3O4 composite was prepared and exhibited good catalytic activity toward the synthesis of S-aryl phosphorothioates. This three-component reaction involved the coupling of in situ generated aryl diazonium salts from aniline, R2P(O)H, and sulfur powder, allowing the facile and direct formation of C(aryl)-S-P bonds. A broad scope of substrates survived the reaction conditions to afford the corresponding

  制备了Cu-BTC @ Fe3O4复合材料，对合成S-芳基硫代磷酸酯具有良好的催化活性。此三组分反应涉及从苯胺，R2P（O）H和硫粉中原位生成的芳基重氮盐偶联，从而可以轻松，直接地形成C（芳基）-SP键。各种各样的底物在反应条件下均能幸存，从而以良好或优异的产率提供相应的产物。而且，该多相催化剂可以在六个循环后被磁回收和再利用而其活性没有显着损失。
• Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S–S and S–P(O) bonds
  作者：Hai Huang、Jeffrey Ash、Jun Yong Kang

  DOI：10.1039/c8ob00908b

  日期：——

  disulfides has been developed under mild reaction conditions. In addition, an aerobic oxidative cross-dehydrogenative coupling (CDC) reaction of thiols with P(O)–H compounds (H-phosphonates and H-phosphine oxide) for the formation of S–P(O) bonds has been demonstrated under the Fe(Pc) catalysis system with a base additive. Control experiments revealed that the use of a base (DIPA) in this system controls

  在温和的反应条件下，已开发出Fe（Pc）催化的硫醇的好氧氧化反应以合成二硫化物。此外，在以下条件下，已证明了硫醇与P（O）-H化合物（H-膦酸酯和H-膦氧化物）的需氧氧化交叉脱氢偶联（CDC）反应可形成S-P（O）键。具有碱性添加剂的Fe（Pc）催化系统。对照实验表明，在该系统中使用碱（DIPA）控制形成硫代磷酸盐的合成途径。
• 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。
• Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates
  作者：Jie Bai、Xiuling Cui、Hui Wang、Yangjie Wu

  DOI：10.1039/c4cc02693d

  日期：——

  An efficient protocol for copper-catalyzed reductive cross-coupling of aryl sulfonyl chlorides with H-phosphonates has been developed. The various S-aryl phosphorothioates were afforded in up to 86% yield for 20 examples. This protocol features high efficiency, wide functional group tolerance, commercially available aryl sulfonyl chlorides as starting materials and base-free conditions.

  已经开发出用于铜催化的芳基磺酰氯与H-膦酸酯的还原性交叉偶联的有效方案。对于20个实施例，以高达86％的收率提供了各种S-芳基硫代磷酸酯。该协议的特点是高效，宽泛的官能团耐受性，可商购的芳基磺酰氯作为起始原料和无碱条件。
• Iodine-catalyzed Sulfenylation of H-phosphonates with Diaryl Disulfides under Metal, Base and Solvent-free Conditions
  作者：Xiang-Mei Wu、Yu-Xiang Hong

  DOI：10.2174/1570178614666161214153431

  日期：2017.2.13

  nitro or halogen substituents including fluoro, chloro and bromo was introduced into the S-aryl phosphorothioates without any problem by employing diaryl disulfides bearing such a group on the phenyl ring at para or meta position, and the corresponding products were between 48-80%. Conclusion: A molecular iodine-catalyzed cross-coupling reaction between phosphonates and diaryl disulfides with H2O2 as

  背景：尽管开发一种简便而有效的S-芳基硫代磷酸酯的制备方法已经引起了广泛的兴趣，但是仍然需要开发一种直接，方便，特别是环境友好的方案，以便在相对温和的条件下获得各种硫代磷酸酯。本文试图研究分子碘，一种在金属，碱和无溶剂条件下在膦酸酯和二芳基二硫化物之间的SP键的构建中的环保试剂。 方法：将二芳基二硫化物（0.5 mmol），H-膦酸酯（2.5 mmol），I2（0.1 mmol）和30％H2O2（0.5 mmol）置于空气中的25 mL两口烧瓶中。将反应混合物在80℃下搅拌12小时。加入水（20mL），然后将混合物用EtOAc（4×10mL）萃取。合并萃取液，用盐水（3×10mL）洗涤，用MgSO 4干燥，过滤，蒸发，并通过硅胶色谱法纯化，得到所需产物，乙酸乙酯/己烷（v / v ＝ 1∶3〜）。 1:10）。通过光谱和分析数据对产物进行表征，并与已知化合物进行比较。 结果：最佳反应条件的