(S)-(-)-isobutyl phenyl sulfoxide | 22456-89-9

• 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: (S)-(-)-isobutyl phenyl sulfoxide
• 英文别名: (S)-(-)-isobutylphenylsulfoxide；(S)-isobutyl phenyl sulfoxide；isobutyl phenyl sulfoxide；[(S)-2-methylpropylsulfinyl]benzene
• CAS: 22456-89-9；67501-04-6；67529-48-0；72174-22-2
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: KTZIDKPRZBGZRZ-LBPRGKRZSA-N

物化性质

• 沸点：
  93-96 °C(Press: 2 Torr)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  bis(2-bromophenyl) sulfoxide 在 正丁基锂 、 S-1,1'-联-2-萘酚 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.67h， 生成 (S)-(-)-isobutyl phenyl sulfoxide
  参考文献：
  名称：

  对称的二芳基亚砜作为二烷基镁化合物的不对称亚磺酰基化试剂

  摘要：

  在-78°C下，当添加1.5当量的（S）-BINOL二锂盐作为促进剂时，伯二烷基镁化合物与二芳基亚砜反应。烷基芳基亚砜导致定量产率最高，ee高达97％。这证明了通过非手性亚磺化剂进行不对称亚磺酰基化的可行性（从烷基2 Mg的角度来看），以及不对称亚砜与镁交换的可行性（从Ar 2 SO角度来看）。

  DOI：

  10.1021/jo502417j

文献信息

• Copper-Catalyzed Asymmetric Oxidation of Sulfides
  作者：Graham E. O’Mahony、Alan Ford、Anita R. Maguire

  DOI：10.1021/jo2026178

  日期：2012.4.6

  Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence

  研究了使用过氧化氢水溶液作为氧化剂的铜催化的芳基苄基和芳基烷基硫化物的不对称硫氧化反应。已经观察到硫化物取代基的空间效应与氧化的对映选择性之间的关系，其中2-萘甲基甲基苯基亚砜的ee高达93％，在这种情况下产率适中（高达30％）。检查了溶剂和配体结构变化的影响，然后使用优化的条件氧化了许多芳基烷基和芳基苄基硫化物，在大多数情况下以极好的收率（高达92％）产生亚砜，并且在室温下具有良好的对映体纯度。某些情况下（高达ee的84％）。
• 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。
• Prochiral Diheteroaryl Sulfoxides and Their Reactions with (<i>S</i>)-Li₂-BINOLate-Activated Diisobutylmagnesium
  作者：Simon Ruppenthal、Reinhard Brückner

  DOI：10.1002/ejoc.201701309

  日期：2018.1.10

  symmetric – i.e. prochiral – diheteroaryl sulfoxides. The latter were treated with a 0.5- or 1.2-fold molar amount of 5:4 mixtures of dilithium (S)-BINOLate and diisobutylmagnesium. This allowed five asymmetric sulfoxide/magnesium exchange reactions to occur. They delivered asymmetric sulfoxides in up to 77 % yield and with up to 88 % ee. Surprisingly, four related diheteroaryl sulfoxides, bis(2-pyridyl)

  5 元环杂环被α-锂化或α-镁化，以便它们攻击SOCl2 或SO(OMe)2，形成对称的——即前手性——二杂芳基亚砜。后者用0.5-或1.2-倍摩尔量的5:4二锂(S)-BINOLate和二异丁基镁的混合物处理。这允许发生五个不对称的亚砜/镁交换反应。他们以高达 77% 的产率和高达 88% 的 ee 提供不对称亚砜。令人惊讶的是，四种相关的二杂芳基亚砜、双（2-吡啶基）亚砜和双（3-吡啶基）亚砜不适合这种交换，而是分解了。
• Chiral<i>N</i>,<i>N</i>′-dioxide–iron(<scp>iii</scp>)-catalyzed asymmetric sulfoxidation with hydrogen peroxide
  作者：Fang Wang、Lili Feng、Shunxi Dong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/d0cc00434k

  日期：——

  enantioselective sulfoxidation of various sulfides has been achieved by a N,N'-dioxide-iron(iii) complex with 35% aq. H2O2 as the oxidant. The utility of the current method was demonstrated by asymmetric gram-scale synthesis of drug molecule (R)-modafinil. Moreover, a possible working mode was provided to elucidate the chiral induction.

  各种硫化物的高度对映选择性的硫氧化反应是通过N，N'-二氧化物-铁（iii）络合物与35％aq。H2O2作氧化剂。药物分子（R）-莫达非尼的不对称克级合成证明了当前方法的实用性。此外，提供了可能的工作模式以阐明手性诱导。
• Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1,2-amino alcohol and an achiral carboxylic acid
  作者：Yuka Kobayashi、Soetrisno、Koichi Kodama、Kazuhiko Saigo

  DOI：10.1016/j.tetasy.2007.11.041

  日期：2008.2

  The enantio selective clathrate formation of alkyl aryl sulfoxides 4 was achieved with dissymmetric one-dimensional helical channels created in two-component hosts consisting of (1R,2S)-2-amino-1,2-diphenylethanol 1 and an achiral carboxylic acid, p-tert-butylbenzoic acid 2, or 2-anthraquinonecarboxylic acid 3. X-ray crystallographic analyses showed that the host framework (1R,2S)-1.3 in the single crystal of a clathrate with methyl p-methylphenyl sulfoxide 4n [(1R,2S)-1.3.4n (single)] maintained a supramolecular helical array as those of the solvent-included single crystals (1R,2S)-1.3-EtOH(single) and (1R,2S)-1-3-H2O.THF(single), while the guest 4n molecules were highly disordered. Moreover, the X-ray powder diffraction pattern of (1R,2S)-1-3-4n(clathrate) obtained through the clathrate formation demonstrated that the molecular arrangements of (1R,2S)-1, 3, and 4n were not the same as those which appeared in (1R,2S)-1.3.4n(single); the channel was enlarged. These results are consistently explained by assuming the dynamic motion of the framework (1R,2S)-1-3 to achieve widely applicable clathrate formation. (c) 2007 Elsevier Ltd. All rights reserved.