(R,S)-bis(p-tolylsulfinyl)ethane | 21884-52-6

• 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: (R,S)-bis(p-tolylsulfinyl)ethane
• CAS: 21884-52-6
• 化学式: C₁₆H₁₈O₂S₂
• 分子量: 306.45
• InChiKey: QHSDSANXJXVJDC-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,2-bis(p-tolylthio)ethane 在 双氧水 、 溶剂黄146 作用下， 生成 (R,S)-bis(p-tolylsulfinyl)ethane
  参考文献：
  名称：

  Crystal structure, proton magnetic resonance spectra, and conformational analysis of 1,4-diphenyl-1,4-dithiabutane 1,4-dioxides and related Meso/dl and Erythro/Threo systems

  摘要：

  DOI：

  10.1021/jo00409a019

文献信息

• Dynamic Kinetic Transformation of Sulfinyl Chlorides:  Synthesis of Enantiomerically Pure <i>C</i>₂-Symmetric Bis-Sulfoxides
  作者：Noureddine Khiar、Cristina S. Araújo、Felipe Alcudia、Inmaculada Fernández

  DOI：10.1021/jo0159183

  日期：2002.1.1

  the synthesis of both isomers of a large number of optically pure C(2)-symmetric bis-sulfoxides have been developed, and their scope and limitations have been assessed. The first one uses as intermediate diastereomerically pure C(2)-symmetric bis-sulfinate esters 6(S(S),S(S)) and 6(R(S),R(S)), obtained by dynamic kinetic resolution of ethane-1,2-bis-sulfinyl chloride 5. A single inducer of chirality

  已经开发了两种模块化和高度收敛的方法，用于合成大量光学纯的C（2）-对称双亚砜的两种异构体，并评估了其范围和局限性。第一个用作中间非对映体纯C（2）-对称双亚磺酸酯6（S（S），S（S））和6（R（S），R（S）），通过动态动力学拆分获得乙烷-1,2-双亚磺酰氯5.单一手性诱导剂，葡萄糖衍生的DAG（双丙酮-D-葡萄糖）1用于非对映异构纯C（2）-对称双亚磺酸盐的对映选择性合成酯，这是由于吡啶和用于催化反应的（i）Pr（2）NEt具有相反的立体定向作用。第二种方法基于光学纯的硫代甲基亚砜的铜催化氧化偶联。可以使用（R（S））-和（S（S））-DAG甲烷亚磺酸酯8R（S）和8S（S）以收敛的方式获得大量甲基亚砜的两种异构体。甲烷亚磺酰氯24的动态动力学拆分也以对映选择性的方式获得了亚甲基磺酸盐8R（S）和8S（S）。由于Horeau的结果，与相应的单体相比，最终的双亚砜具有更高的对映选择性。
• Vanadium catalyzed enantioselective oxidation of sulfides: easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides
  作者：Jacek Skarżewski、Elżbieta Ostrycharz、Renata Siedlecka

  DOI：10.1016/s0957-4166(99)00374-2

  日期：1999.9

  A facile and selective method for the title transformation is described. The two-phase oxidation of bis-sulfides with hydrogen peroxide catalyzed by vanadium complex of chiral Schiff base leads to the corresponding chiral mono- and bis-sulfoxides. In the case of 1,2-bis(arylthio)ethanes the respective optically active bis-sulfoxides are formed in up to over 95% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Thermodynamic Resolution and Enantioselective Synthesis of <i>C</i>₂-Symmetric Bis-sulfoxides Based on Chiral Iridium(III) Complexes
  作者：Li-Ping Li、He-Long Peng、Bao-Hui Ye

  DOI：10.1021/acs.inorgchem.9b01682

  日期：2019.9.16

  Enantiopure Λ-[Ir(dfppy)₂(MeCN)₂](PF₆) and Δ-[Ir(dfppy)₂(MeCN)₂](PF₆) (where dfppy is (4,6-difluoropheny)pyridine) were demonstrated to preferentially react with (S,S)-1,2-bis(arylsulfinyl)ethane and (R,R)-1,2-bis(arylsulfinyl)ethane, respectively, under thermodynamic equilibrium. Sequential treatment of Λ-[Ir(dfppy)₂(MeCN)₂](PF₆) and Δ-[Ir(dfppy)₂(MeCN)₂](PF₆) with C₂-symmetric bis-sulfoxides led to diastereoselective formation of the corresponding diastereomers Λ-[Ir(dfppy)₂(R,R)-bis-sulfoxide)](PF₆) in 90-92% and Δ-[Ir(dfppy)₂(S,S)-bis-sulfoxide)](PF₆) in 88-90%, respectively. The uncoordinated (R,S)-bis-sulfoxides were afforded in 45% with >97% de values. Enantiopure (S,S)-bis-sulfoxides and (R,R)-bis-sulfoxides were respectively obtained by the release of sulfoxide ligands from the corresponding complexes in the presence of glycine in yields of 20-21% with 97-99% ee values. The enantioreceptors Λ-[Ir(dfppy)₂(MeCN)₂](PF₆) and Δ-[Ir(dfppy)₂(MeCN)₂](PF₆) can be recycled and reused in the next reaction cycle. Moreover, a protocol for asymmetric oxidation of prochiral bis-sulfide into enantiopure C₂ symmetric bis-sulfoxide was also developed in a high enantioselectivity. The absolute configurations at the metal centers and sulfur atoms were determined by X-ray crystallography.