benzyl t-butyl sulfoxide | 2844-08-8

• 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: benzyl t-butyl sulfoxide
• 英文别名: (R)-benzyl t-butyl sulphoxide；S_R-tert-butyl phenylmethyl sulfoxide；(R)-(-)-tert-butyl benzyl sulfoxide；(R)-((tert-butylsulfinyl)methyl)benzene；[(R)-tert-butylsulfinyl]methylbenzene
• CAS: 2844-08-8
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: HOHHGPSMIBONTK-CYBMUJFWSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  347.6±21.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl t-butyl sulfoxide 在 正丁基锂 、 重水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 [[(R)-tert-butylsulfinyl]-deuteriomethyl]benzene
  参考文献：
  名称：

  Stereochemistry of the .alpha.-sulfinyl phenylmethyl carbanion. Reevaluation of the configuration

  摘要：

  DOI：

  10.1021/jo00384a006
• 作为产物：
  描述：

  benzyl t-butyl sulfide 生成 benzyl t-butyl sulfoxide
  参考文献：
  名称：

  FUJIMORI, KEN;MATSUURA, TAKAHARU;MIKAMI, AKIHIRO;WATANABE, YOSHIHITO;OAE,+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 1435-1440

  摘要：

  DOI：

文献信息

• Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides
  作者：Graham E. O'Mahony、Kevin S. Eccles、Robin E. Morrison、Alan Ford、Simon E. Lawrence、Anita R. Maguire

  DOI：10.1016/j.tet.2013.08.063

  日期：2013.11

  in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast

  已经研究了在铜催化的芳基苄基，芳基烷基和烷基苄基硫化物的不对称氧化中的立体效应和电子效应。直接连接到硫上的芳基的存在对于提供具有高对映选择性的亚砜是必不可少的，2-萘基苄基亚砜具有高达97％ee的电子，这是迄今为止铜催化的不对称亚砜氧化所达到的最高对映选择性。与此相反，苄基取代基可以通过在空间上可比基团与对映选择性上没有影响取代。的取代的芳基苄基硫化物铜 - 介导的氧化导致显示在相当或更低的对映选择性，以与未取代的苄基苯基硫醚获得的那些适度立体和电子效应。
• Diastereomeric sulfinates derived from (l)-N-methylephedrine: synthesis, applications and rearrangements
  作者：Józef Drabowicz、Bogdan Bujnicki、Paolo Biscarini、Marian Mikołajczyk

  DOI：10.1016/s0957-4166(99)00336-5

  日期：1999.8

  The reaction of sulfinyl chlorides with (l)-N-methylephedrine alone or in the presence of tertiary amines was found to produce diastereomeric sulfinates with diastereomeric purities up to 90%. The diastereomeric ratio is strongly influenced by the nature of substituents on the sulfinyl chlorides and to some extent by the reaction conditions. In a few cases, the pure diastereomers were isolated by chromatography

  发现亚磺酰氯与（1）-N-甲基麻黄碱单独或在叔胺存在下的反应产生具有高达90％的非对映体纯度的非对映体亚磺酸盐。非对映体比率受亚磺酰氯上取代基的性质的强烈影响，并且在一定程度上受反应条件的影响。在少数情况下，通过色谱法分离纯的非对映异构体，并用于制备旋光性亚砜。还讨论了硅胶催化的亚磺酸盐重排为相应的砜。
• Stereochemisty of oxygenation of organic sulphides with pig liver microsomal FAD-containing mono-oxygenase: comparison with cytochrome P-450PB oxidations
  作者：Ken Fujimori、Takaharu Matsuura、Akihiro Mikami、Yoshihito Watanabe、Shigeru Oae、Takashi Iyanagi

  DOI：10.1039/p19900001435

  日期：——

  The enantiotopic differentiating ability of pig liver microsomal FAD-containing mono-oxygenase (EC 1.14.13.8) in the oxygenation of nine unsymmetrical sulphides has been investigated. By this enzymatic oxygenation, the sulphides are converted into the corresponding optically active sulphoxides with varying degrees of enantiomeric excess (96–12%).

  研究了猪肝微粒体中含FAD的单加氧酶（EC 1.14.13.8）在九种不对称硫化物的氧化中对映体的分化能力。通过这种酶促氧化作用，硫化物被转化为相应的旋光性亚砜，其对映体过量程度不同（96-12％）。
• Diastereoconvergent synthesis of chiral sulfoxides containing vicinal amino alcohol framework
  作者：Yan-Xue Zhang、Ling-Yan Chen、Bang-Guo Wei

  DOI：10.1016/j.tetlet.2019.151466

  日期：2020.2

  diastereoconvergent synthesis of chiral sulfoxides containing vicinal amino alcohol framework has been achieved in moderate to good yield with up to 99:1 dr. Different from the previous work, the stereochemistry of the new chiral center was determined solely by the configuration of benzyl tert-butyl sulfoxide, while both the chiral sulfinyl group and the tert-butyldimethylsilyl ether (α-OTBS) group at the α-position

  已经成功地以中等至良好的收率（高达99：1 dr）实现了含有邻位氨基醇骨架的手性亚砜的高度非对映聚合反应。与以前的工作不同，新的手性中心的立体化学仅由苄基叔丁基亚砜的构型决定，而手性亚磺酰基和叔丁基二甲基甲硅烷基醚（α- OTBS）均位于亚胺不参与立体声诱导。该方法还提供了吡咯烷酮的手性构件的有效合成。
• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.