(S_S)-menthyl p-toluenesulfinate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S_S)-menthyl p-toluenesulfinate
• 英文别名: (5-methyl-2-propan-2-ylcyclohexyl) (S)-4-methylbenzenesulfinate
• 化学式: C₁₇H₂₆O₂S
• 分子量: 294.458
• InChiKey: NQICGNSARVCSGJ-PHQZTZODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S_S)-menthyl p-toluenesulfinate 在 苄基三乙基氯化铵 sodium hydroxide 、 正丁基锂 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 生成
  参考文献：
  名称：

  Stereospecific Synthesis ofS-Phenyl-S-(sulfinylmethyl)-sulfoximines and their Stereoselective Alkylation under the Influence of the Two Chiral Centers

  摘要：

  DOI：

  10.1055/s-1982-29937
• 作为产物：
  描述：

  对甲苯亚磺酸 在 氯化亚砜 、 silica gel 作用下， 反应 0.77h， 生成 (S_S)-menthyl p-toluenesulfinate
  参考文献：
  名称：

  ONE-POT AND SIMPLE REACTION FOR THE SYNTHESIS OF ALKYL p-TOLUENESULFINATE ESTERS UNDER SOLID-PHASE CONDITIONS

  摘要：

  A manipulatively one-pot and rapid method for the synthesis of alkyl p-toluenesulfinate esters 1 from p-toluenesulfinic acid, supported thionyl chloride on silica gel and aliphatic alcohols in solid phase conditions is described.

  DOI：

  10.1080/10426500008043672

文献信息

• P-Stereogenic Phosphonates via Dynamic Kinetic Resolution: A Route towards Enantiopure Tertiary Phosphine Oxides
  作者：Aabid Mohd、Thippani Anitha、Kallu Rajender Reddy、Joanna Wencel-Delord、Françoise Colobert

  DOI：10.1002/ejoc.201901475

  日期：2019.12.31

  A DKR scenario towards O–P coupling reaction involving an easily accessible enantiopure phenol bearing a chiral sulfinyl auxiliary and racemic H‐phosphinates. The enantiopure P‐stereogenic phosphonates bearing two different alkoxy groups are valuable precursors to reach privileged ligands such as PAMPO.

  DKR方案涉及到O-P偶联反应，涉及易于获得的对映纯苯酚，其带有手性亚磺酰基助剂和外消旋H-次膦酸酯。带有两个不同烷氧基的对映体纯对映体膦酸酯是有价值的前体，可用于获得优先配体，例如PAMPO。
• Asymmetric Synthesis of Aryl Benzyl Sulfoxides by Vanadium-Catalysed Oxidation: A Combination of Enantioselective Sulfide Oxidation and Kinetic Resolution in Sulfoxide Oxidation
  作者：Pádraig Kelly、Simon E. Lawrence、Anita R. Maguire

  DOI：10.1002/ejoc.200600320

  日期：2006.10

  Enantioselective vanadium-catalysed oxidation of aryl benzyl sulfides using Bolm’s procedure is accompanied by kinetic resolution in the oxidation of the resulting sulfoxides which enhances the enantiopurities of the sulfoxides recovered (typically >90 % ee), albeit with an associated reduction in yield. The effects of ligand, solvent and reaction conditions are discussed in detail.(© Wiley-VCH Verlag

  使用 Bolm 程序对芳基苄基硫化物进行对映选择性钒催化氧化伴随着所得亚砜氧化的动力学拆分，这提高了回收的亚砜的对映纯度（通常 >90% ee），尽管伴随着产率的降低。详细讨论了配体、溶剂和反应条件的影响。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Stereoselectivity Switch in the Trapping of Polar Organometallics with Andersen’s Reagent—Access to Highly Stereoenriched Transformable Biphenyls
  作者：Julien Bortoluzzi、Vishwajeet Jha、Guillaume Levitre、Mickaël J. Fer、Jordan Berreur、Géraldine Masson、Armen Panossian、Frédéric R. Leroux

  DOI：10.1021/acs.joc.8b00648

  日期：2018.8.3

  The trapping of racemic polar carbometallic species with (−)-menthyl (SS)-p-toluenesulfinate (Andersen’s reagent) typically proceeds with a very low level of resolution. In this paper, we describe a strategy that allows access to highly atropo-enriched and functionalizable biphenyls by means of Andersen’s reagent under kinetic resolution conditions. In particular, useful enantiopure 2-iodobiphenyls

  （ - ） -薄荷（消旋极carbometallic物种与捕捉小号小号） - p -toluenesulfinate（安徒生试剂）通常进行的分辨率非常低的水平。在本文中，我们描述了一种策略，该策略允许在动力学分辨率条件下通过安徒生（Andersen）试剂获得高度富含阿托品和可官能化的联苯。特别地，可获得有用的对映纯2-碘联苯，并将其用于具有挑战性的高价碘催化的氧化反应中。
• Towards the enantioselective synthesis of axially chiral cyclic bis(bibenzyls) through sulfoxide-controlled diastereoselective Suzuki coupling
  作者：Petra Schmitz、Marcus Malter、Gregor Lorscheider、Christina Schreiner、Aude Carboni、Sabine Choppin、Françoise Colobert、Andreas Speicher

  DOI：10.1016/j.tet.2015.12.052

  日期：2016.8

  Natural macrocyclic bis(bibenzyls) exhibiting configurationally stable axially chiral biaryls are of high interest from a structural as well as from a synthetic point of view. An enantiopure sulfinyl auxiliary controlling an atropo-diastereoselective biaryl Suzuki coupling reaction has been investigated and promising results for the preparation of the biaryl moiety of cyclic bis(bibenzyls) like isoplagiochins

  从结构以及从合成的观点来看，表现出构型稳定的轴向手性联芳基的天然大环双（联苄基）备受关注。已经研究了控制对映体-非对映选择性联芳基Suzuki偶联反应的对映体纯亚磺酰基助剂，并获得了制备环状双（联苄基）如异斜烷C或D的联芳基部分的有希望的结果。此外，讨论了解释过渡态期间的立体选择性和包括双重立体分化的替代效应的模型。
• Atroposelective Synthesis of Isoriccardin C through a C−H Activated Heck Type Macrocyclization
  作者：Lisa Marx、Daniel Lamberty、Sabine Choppin、Françoise Colobert、Andreas Speicher

  DOI：10.1002/ejoc.202100017

  日期：2021.3.5

  A chiral sulfinyl auxiliary group in ortho‐position of a biaryl axis is directing in the adjacent aryl moiety an atropo‐diastereoselective ortho’‐Fujiwara‐Moritani Heck coupling with dynamic kinetic resolution and can finally be transformed into a hydroxyl function of a natural occurring cyclophane type bisbibenzyl.

  在联芳基轴邻位的手性亚磺酰基辅助基团在相邻的芳基部分中引导具有动态动力学拆分的对位-非对映选择性邻'-藤原-莫里塔尼·赫克偶联，最终可以转化为天然存在的环烷的羟基官能团双联苄基类型。