1,2-bis(phenylsulfinyl)ethane | 28045-36-5

• 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: 1,2-bis(phenylsulfinyl)ethane
• 英文别名: meso-1,2-bis-benzenesulfinyl-ethane；meso-1,2-Bis-benzolsulfinyl-aethan；[(S)-2-[(S)-phenylsulfinyl]ethylsulfinyl]benzene
• CAS: 28045-36-5
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: CSZMCUCIIIAHQD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  neodymium(III) perchlorate 、 1,2-bis(phenylsulfinyl)ethane 以 乙醇 、 氯仿 为溶剂， 生成 {Nd2(rac-bis(phenylsulphinyl)ethane)7(perchlorate)2}(perchlorate)4*4H2O
  参考文献：
  名称：

  双（苯基亚磺酰基）乙烷的镧系高氯酸盐络合物

  摘要：

  摘要镧系高氯酸盐与外消旋双（苯基亚磺酰基）乙烷的络合物：[Ln2（L）7（ClO4）2]（ClO4）4·nH2O（其中Ln = La-Nd，Sm，Gd-Er，Yb； n = 0， 4）通过相应的高氯酸镧与外消旋双（苯基亚磺酰基）乙烷的反应制备，并通过元素分析，电导率，磁化率，IR和电子光谱以及热分析进行表征。

  DOI：

  10.1016/s0277-5387(00)83622-0
• 作为产物：
  描述：

  1,2-联苯硫基乙烷 在 (S)-(-)-N-(3,5-di-tert-butylsalicylidene)-tert-lucinol 、 vanadyl acetylacetonate 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 生成 1,2-bis(phenylsulfinyl)ethane
  参考文献：
  名称：

  Skarzewski, Jacek; Ostrycharz, Elzbieta; Siedlecka, Renata, Journal of Chemical Research, Miniprint, 2001, # 7, p. 743 - 757

  摘要：

  DOI：

文献信息

• Complexes of disulphoxides with triphenyltin chloride
  作者：Carlos A.L. Filgueiras、Celio Celso、Eva V. Marques、Brian F.G. Johnson

  DOI：10.1016/s0020-1693(00)87309-0

  日期：1982.1

  Six new complexes have been prepared with Ph3SnCl and the disulphoxides rac-(PrSOCH2)2, rac-cis-PhSOCH*CHSOPh, meso-(PhSO)2CH2, rac-(PhSO)2CH2, meso-(PhSOCH2)2, and rac-(PhSCOCH2)2. The first of these complexes is a bridged 2:1 acid: base adduct, whereas the others seem to be 1:1 chelated compounds. Several features of the complexes were studied by IR spectroscopy, X-Ray crystallography and NMR spectroscopy

  已用Ph3SnCl和二硫化物rac-（PrSOCH2）2，rac-cis-PhSOCH *CHSOPh，内消旋-（PhSO）2CH2，rac-（PhSO）2CH2，内消旋（PhSOCH2）2和rac制备了六个新的配合物-（PhSCOCH2）2。这些复合物中的第一个是桥接的2：1酸：碱加合物，而其他似乎是1：1螯合的化合物。通过IR光谱，X射线晶体学和NMR光谱研究了配合物的几个特征。
• Stereochemistry and crystal structures of triphenyltin chloride complexes with bis(phenylsulfinyl)ethane
  作者：F.C. Zhu、P.X. Shao、X.K. Yao、R.J. Wang、H.G. Wang

  DOI：10.1016/s0020-1693(00)84669-1

  日期：1990.5

  Abstract 2:1 Complexes of triphenyltin chloride (TPTC) with meso,rac-bis(phenylsulfinyl)ethane (meso,rac-BPSE) have been prepared in the form of crystals suitable for crystallography. The complex (TPTC)2·meso-BPSE is monoclinic with a = 8.813(2), b = 22.920(5), c = 11.929(4) A, β = 104.16(2)°, space group P21/n. (TPTC)2·rac-BPSE is an identical complex with (TPTC)2·meso-BPSE and configurational inversion

  摘要2：1制备了三苯基氯化锡（TPTC）与内消旋-rac-双（苯基亚磺酰基）乙烷（meso，rac-BPSE）的配合物，其晶体形式适合于晶体学。复数（TPTC）2·meso-BPSE是单斜晶，a = 8.813（2），b = 22.920（5），c = 11.929（4）A，β= 104.16（2）°，空间群P21 / n。（TPTC）2·rac-BPSE与（TPTC）2·meso-BPSE是相同的络合物，并且当配体与TPTC反应时，rac-BPSE中的一个硫原子发生构型反转。
• Farina et al., Gazzetta Chimica Italiana, 1959, vol. 89, p. 1548,1553
  作者：Farina et al.

  DOI：——

  日期：——
• 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.