(S)-1-(propylsulfinyl)-4-methylbenzene | 129016-19-9

• 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)-1-(propylsulfinyl)-4-methylbenzene
• 英文别名: 1-methyl-4-[(S)-propylsulfinyl]benzene
• CAS: 129016-19-9
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: PAKKXSULXNLYDV-LBPRGKRZSA-N

物化性质

• 沸点：
  310.5±21.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(propylsulfinyl)-4-methylbenzene 在 N-氯代丁二酰亚胺 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-((R)-1-Chloro-propane-1-sulfinyl)-4-methyl-benzene
  参考文献：
  名称：

  Highly Stereoselective Nucleophilic Epoxidation of Simple Vinyl Sulfoxides

  摘要：

  DOI：

  10.1021/jo972358s
• 作为产物：
  描述：

  (R)-p-tolyl vinyl sulfoxide 在 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 (S)-1-(propylsulfinyl)-4-methylbenzene
  参考文献：
  名称：

  溴化乙烯基芳基亚砜与格氏试剂的对映体特异性反应产生的旋光亚砜

  摘要：

  使旋光的溴乙烯芳基亚砜与苯基或烷基镁化合物反应，制得旋光的二芳基或芳基烷基亚砜，且构型反转。发现该过程的对映特异性为98–100％。

  DOI：

  10.1016/s0040-4039(00)61207-8

文献信息

• Enzymatic kinetic resolution of chiral sulfoxides – an enantiocomplementary approach
  作者：Vladimír Nosek、Jiří Míšek

  DOI：10.1039/c9cc05470g

  日期：——

  A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.

  描述了一种新的用于制备手性亚砜的酶促测定方法，该方法与甲硫氨酸亚砜还原酶A（MsrA）的已知的（S）-对映异构体还原活性是对映体互补的。为此，我们利用了DMSO还原酶（DmsABC），该酶最近被我们发现在固定相大肠杆菌中高度上调。
• Iron-Catalyzed Imidative Kinetic Resolution of Racemic Sulfoxides
  作者：Jun Wang、Marcus Frings、Carsten Bolm

  DOI：10.1002/chem.201303850

  日期：2014.1.20

  resolution of racemic sulfoxides requires either custom substrates or shows moderate enantioselectivity, leading to achiral coproducts (such as sulfones) as an intrinsic part of the process. A new strategy is demonstrated that allows the resolution of racemic sulfoxides through catalytic asymmetric nitrene‐transfer reactions. This approach gives rise to both optically active sulfoxides and highly enantioenriched

  外消旋亚砜的动力学拆分需要定制的底物或显示适度的对映选择性，从而导致非手性副产物（如砜）成为该过程的内在部分。展示了一种新策略，该策略可通过催化不对称腈转移反应拆分消旋亚砜。该方法同时产生了旋光活性亚砜和高度对映体富集的亚砜亚胺。通过使用手性铁催化剂和容易获得的碘丁烷试剂，在非常实际的反应条件下已经获得了高选择性因子。关于底物的范围，值得注意的是，外消旋亚砜的这种前所未有的酰亚胺化动力学拆分提供了以高度对映体富集的形式获得芳基烷基和二烷基亚砜基的方法。
• A novel route to enantiomerically pure sulfoxides through displacement of a carbon leaving group
  作者：Cosimo Cardellicchio、Antonio Iacuone、Francesco Naso、Paolo Tortorella

  DOI：10.1016/0040-4039(96)01264-6

  日期：1996.8

  Enantiomerically pure sulfoxides were produced by reaction of dimethyl (S)-p-tolyl-sulfinylmethylphosphonate with the suitable Grignard reagents. Yields up to 75% were obtained.

  通过使（S）-对甲苯基-亚磺酰基甲基膦酸二甲酯与合适的格氏试剂反应生成对映体纯的亚砜。获得了高达75％的产率。
• Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enantiomerically pure sulfoxides
  作者：I. Fernandez、N. Khiar、J. M. Llera、F. Alcudia

  DOI：10.1021/jo00051a022

  日期：1992.12

  Diacetone-D-glucose (DAG), a commercially available, sugar-derived secondary alcohol, was found to react with alkane- and arenesulfinyl chlorides in the presence of a tertiary amine in a very useful manner. When i-Pr2Net is used as the base, (-)-(S)-alkane- and arenesulfinates are obtained in 50-90% yield with 89-greater-than-or-equal-to 95% de. Simply changing the base from i-Pr2NEt to Py affords (+)-(R)-alkane- and arenesulfinates in 56-87% yield with 70-greater-than-or-equal-to 95% de. The de's were determined by H-1 NMR. Optically pure alkane- and arenesulfinates are obtained either by recrystallization or by column chromatography. These sulfinates were transformed into various enantiomerically pure sulfoxides (alkyl alkyl and alkyl aryl) by reaction with different Grignard reagents. This new methodology is cheap, quick, and very convenient when both enantiomers of a given sulfoxide are needed enantiomerically pure. The influence of the solvent, as well as the effect of other types of bases, on the stereochemical course of the reaction has been evaluated, and a possible origin of the diastereoselectivity is discussed. Other optically pure secondary alcohols are used m the same reaction, and the comparison of their behavior with that of DAG is also reported.