1-(t-BuMe2Si)-2-(phenylthio)ethyl ether | 450409-95-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(t-BuMe2Si)-2-(phenylthio)ethyl ether
• 英文别名: [[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]thio]benzene；tert-butyl-dimethyl-(2-phenylsulfanylethoxy)silane
• CAS: 450409-95-7
• 化学式: C₁₄H₂₄OSSi
• 分子量: 268.495
• InChiKey: CVZDAGCRTGDTDF-UHFFFAOYSA-N

物化性质

• 沸点：
  307.6±25.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(t-BuMe2Si)-2-(phenylthio)ethyl ether 在 manganese(II) sulfate 、 双氧水 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以86%的产率得到(2-Benzenesulfonyl-ethoxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  简单，经济，环保的砜合成

  摘要：

  在NaHCO 3缓冲溶液的存在下，使用催化量的MnSO 4 ·H 2 O（1 mol％）和30％H 2 O 2进行了官能化硫化物的化学选择性硫氧化反应。在15分钟内以定量收率将芳香族和脂肪族硫化物氧化为砜。在这些温和和绿色的反应条件下，可以耐受不同的官能团，包括双键，醇，THP和TBDMS基团的醚。

  DOI：

  10.1016/s0040-4039(02)00598-1
• 作为产物：
  描述：

  2-苯硫基乙醇 、 t-butyldimethylsilane 在 钯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 1-(t-BuMe2Si)-2-(phenylthio)ethyl ether
  参考文献：
  名称：

  A Catalytic Synthesis of Thiosilanes and Silthianes:  Palladium Nanoparticle-Mediated Cross-Coupling of Silanes with Thio Phenyl and Thio Vinyl Ethers through Selective Carbon−Sulfur Bond Activation

  摘要：

  Palladium nanoparticles generated in situ from N,N-dimethyl-acetamide (DMA) solutions of PdX2 (X = Cl-, OAc-, OCOCF3-) or Pd-2(dba)(3) by reduction with alkyl silanes R3SiH (R = Me, Et, i-Pr, t-Bu) are selective catalysts for the cross-coupling of the silanes R3SiH with phenyl and vinyl thioethers forming the corresponding thiosilanes and silthianes in high yields and under mild conditions. The method is applicable to phenyl thioglycosides, giving access to thiosilyl glycosides a new class of sugar derivatives.

  DOI：

  10.1021/ja049386u

文献信息

• Radical reaction of S-phenyl chlorothioformate with alkyl iodides: free radical-mediated carboxylation approach
  作者：Sunggak Kim

  DOI：10.1039/a800664d

  日期：——

  Free radical-mediated carboxylation is achieved by treatment of alkyl iodides with S-phenyl chlorothioformate and bis(tributyltin) with irradiation at 300 nm.

  通过在300 nm波长照射下，使用S-苯基氯硫代甲酸酯和双(三丁基锡)处理烷基碘化物，实现了自由基介导的羧化反应。
• Nickel-Catalyzed C–S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers
  作者：Yu-Zhong Yang、Yang Li、Gui-Fen Lv、De-Liang He、Jin-Heng Li

  DOI：10.1021/acs.orglett.2c01954

  日期：2022.7.22

  A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C(sp3)–S bond, and features exquisite

  开发了一种镍催化的烷基卤化物与芳基硫硅烷的 C-S 还原交叉偶联，用于生产烷基芳基硫醚。该反应由芳基硫硅烷的 umpolung 转变引发，然后与卤代烷发生 C-S 还原交叉偶联，将亲电烷基控制在亲电硫原子上，然后构建 C(sp 3 )-S 键，具有出色的化学选择性，对多种官能团具有优异的耐受性，并广泛应用于生物相关分子的后期修饰。
• Nickel‐catalyzed umpolung C S radical reductive cross coupling of S‐(trifluoromethyl)arylsulfonothioates with alkyl halides
  作者：Yu-Zhong Yang、Gui-Fen Lv、Ming Hu、Yang Li、Jin-Heng Li

  DOI：10.1016/j.cclet.2023.108590

  日期：2023.11

  A new cooperative nickel reductive catalysis and N,N-dimethylformamide-mediated strategy for umpolung CS radical reductive cross coupling of S-(trifluoromethyl)arylsulfonothioates with alkyl halides to produce alkyl aryl thioethers is described. This reaction features excellent selectivity, wide functionality tolerance, broad substrate scope, and facile late-stage modification of biologically relevant

  描述了一种新的协同镍还原催化和N,N-二甲基甲酰胺介导的策略，用于S- (三氟甲基)芳基硫代磺酸酯与烷基卤的 C S 自由基还原交叉偶联生产烷基芳基硫醚。该反应具有优异的选择性、广泛的功能耐受性、广泛的底物范围以及易于对生物相关分子进行后期修饰。机理研究认识到，通过用 Sn 热诱导 DMF还原，最初生成酰胺自由基阴离子，然后进行反极化还原和亲核磺酰基部分的单电子转移，形成巯基自由基并与 Ni 0 /Ni I /Ni III接合/Ni I催化循环。
• Simple, economical and environmentally friendly sulfone synthesis
  作者：Diego A. Alonso、Carmen Nájera、Montserrat Varea

  DOI：10.1016/s0040-4039(02)00598-1

  日期：2002.5

  Chemoselective sulfur oxidation of functionalized sulfides was developed using catalytic amounts of MnSO4·H2O (1 mol%) and 30% H2O2 in the presence of a buffer solution of NaHCO3. Aromatic and aliphatic sulfides were oxidized to sulfones in quantitative yields in 15 min. Different functional groups including double bonds, alcohols, ethers of THP and TBDMS groups were tolerated under these mild and

  在NaHCO 3缓冲溶液的存在下，使用催化量的MnSO 4 ·H 2 O（1 mol％）和30％H 2 O 2进行了官能化硫化物的化学选择性硫氧化反应。在15分钟内以定量收率将芳香族和脂肪族硫化物氧化为砜。在这些温和和绿色的反应条件下，可以耐受不同的官能团，包括双键，醇，THP和TBDMS基团的醚。
• A Catalytic Synthesis of Thiosilanes and Silthianes:  Palladium Nanoparticle-Mediated Cross-Coupling of Silanes with Thio Phenyl and Thio Vinyl Ethers through Selective Carbon−Sulfur Bond Activation
  作者：Mee-Kyung Chung、Marcel Schlaf

  DOI：10.1021/ja049386u

  日期：2004.6.1

  Palladium nanoparticles generated in situ from N,N-dimethyl-acetamide (DMA) solutions of PdX2 (X = Cl-, OAc-, OCOCF3-) or Pd-2(dba)(3) by reduction with alkyl silanes R3SiH (R = Me, Et, i-Pr, t-Bu) are selective catalysts for the cross-coupling of the silanes R3SiH with phenyl and vinyl thioethers forming the corresponding thiosilanes and silthianes in high yields and under mild conditions. The method is applicable to phenyl thioglycosides, giving access to thiosilyl glycosides a new class of sugar derivatives.