(R)-2-naphthyl methyl sulfoxide | 35330-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-naphthyl methyl sulfoxide
• 英文别名: (R)-(+)-2-(methylsulfinyl)naphthalene；(R)-(+)-methyl 2-naphthyl sulfoxide；(R)-2-(methylsulfinyl)naphthalene；(R)-2-methanesulfinylnaphthalene；(R)-methyl 2-naphthyl sulfoxide；(R)-methyl 2-naphthylsulfoxide；2-[(R)-methylsulfinyl]naphthalene
• CAS: 35330-76-8；101541-53-1；114129-50-9；18690-03-4
• 化学式: C₁₁H₁₀OS
• 分子量: 190.266
• InChiKey: VBRDXOMJHRAPSU-CYBMUJFWSA-N

物化性质

• 沸点：
  384.2±11.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (R)-2-naphthyl methyl sulfoxide 以 乙腈 为溶剂， 生成 2-(甲基亚磺酰基)萘
  参考文献：
  名称：

  Photophysics and Photostereomutation of Aryl Methyl Sulfoxides¹

  摘要：

  The effect of a methanesulfinyl group on the photophysics of several aromatic chromophores is reported. The spectroscopic singlet and triplet energies are affected only modestly, compared to that parent arenes, but the fluorescence yields fall by at least 1 order of magnitude. Fluorescence lifetimes are short. Fluorescence enhancements are observed on cooling the sulfoxides from room temperature to 77 K. High quantum yields of stereomutation are reduced as the temperature drops. There is not a consistent effect on triplet or phosphorescence yields. It is proposed that these results are consistent with a nonradiative pathway for deactivation of the singlet that results in stereomutation. A modest activation energy of a few kcal/mol is estimated for the photochemical racemization of 1-methanesulfinylpyrene

  DOI：

  10.1021/jo0056141
• 作为产物：
  描述：

  2-(甲硫基)萘 在 MKKRIGIVGAGTAGLHLGLFLRQHDHDVTVYTDRQPDEYAGLRLLNTVAHHAVTVQREVDLGVNEWPSDEFGYFGHYYYVGGPQPMRFYGDLKAPSRAVDYRLYQPMLMRALEARGGKFSYDAVSVEDLESLSDQYDLLVVCTGKNSLGQLFEKQPENSPFEKPQRALCVGLFKGIKEAPIRAVTMSFSPGHGELIEIPTLSFNGMTTALVLENHIGGFRNGHATLKNGKTIIGLGDVQATVDPVLGQGANMASHAAWILGEEILSHSVYDHRFCEHLERRRQDRVLCATRWTNFTMGALQALPPEFIAFLQVLSQSREMADEFTDNFNYPERQWDRFSSPERIGHWCSQYAPTIAA 、 还原型辅酶II(NADPH)四钠盐 、 葡萄糖 、 MSDKIKHVTDASFEADVLQAQGPVLVDYWAEWCGPCKMIAPVLDDIAATYEGKLTVAKLNIDENQETPAKHGVRGIPTLMLFKNGNVEATKVGALSKSQLAAFLDAHL 、 MSEVRHSRVIILGSGPAGYSAAVYAARANLKPLLITGMQAGGQLTTTTEVDNWPGDPHGLTGPALMQRMQEHAERFETEIVFDHINAVDLANKPFTLQGDSGKYTCDALIIATGASARYLGLPSEETFMGKGVSACATCDGFFYRNKPVAVVGGGNTAVEEALYLANIASKVTLVHRRDTFRAEKILVDKLHARVAEGKIELKLNATLDEVLGDNMGVTGARLKNNDGSSDEIKVDGVFIAIGHTPNTSLFEGQLTLKDGYLVVNGGREGNATATNIEGVFAAGDVADHVYRQAITSAGAGCMAALDVERYLDGLANASF 、 MVLRSEILVNKNVMPTAEQALPGRETPMSLPEFHYVFKDTPLLGPFFEGAIDFAIFGLGCFWGAERRFWQREGVVSTVVGYAGGFTPHPTYEEVCSGLTGHTEVVLVVFDKDRVSYRELLAMFWELHNPTQGMRQGNDIGTQYRSAIYCTSPEQLEQAKASRDAFQAELSKAGFGEITTEIDQAPTVYFAEAYHQQYLAKNPDGYCGIGGTGVCLPPSLQGN 、 MYPDLKGKVVAITGAASGLGKAMAIRFGKEQAKVVINYYSNKQDPNEVKEEVIKAGGEAVVVQGDVTKEEDVKNIVQTAIKEFGTLDIMINNAGLENPVPSHEMPLKDWDKVIGTNLTGAFLGSREAIKYFVENDIKGNVINMSSVHEVIPWPLFVHYAASKGGIKLMTETLALEYAPKGIRVNNIGPGAINTPINAEKFADPKQKADVESMIPMGYIGEPEEIAAVAAWLASKEASYVTGITLFADGGMTQYPSFQAGRG 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 以93%的产率得到(R)-2-naphthyl methyl sulfoxide
  参考文献：
  名称：

  具有辅助因子再生的多酶氧化还原系统用于亚砜的循环脱消旋

  摘要：

  建立了辅因子再生的多酶循环去外消旋体系，用于制备对映体纯亚砜。通过蛋氨酸亚砜还原酶 (Msr)、苯乙烯单加氧酶 (SMO) 和其他三种辅助酶（Trx、Trx-R 和 GDH）的级联催化，以 >90% 的产率和 >90%的ee制备手性亚砜。

  DOI：

  10.1002/anie.202209272

文献信息

• Catalytic Enantioselective Oxidation of Bulky Alkyl Aryl Thioethers with H2O2 over Titanium-Salan Catalysts
  作者：Konstantin P. Bryliakov、Evgenii P. Talsi

  DOI：10.1002/ejoc.201100557

  日期：2011.8

  procedure for the oxidation of bulky (preferably aryl benzyl substituted) thioethers with hydrogen peroxide in good to high yields and enantioselectivities (up to 98.5 % ee) is reported. The high optical yields are achieved in a tandem stereoconvergent enantioselective oxidation and kinetic resolution process. A reasonable balance between the sulfoxide yield and enantioselectivity could be found by varying

  报道了一种用过氧化氢以良好至高产率和对映选择性（高达 98.5% ee）氧化大体积（优选芳基苄基取代）硫醚的简单有效的催化程序。在串联立体会聚对映选择性氧化和动力学拆分过程中实现了高光学产率。通过改变浓度和温度可以找到亚砜产率和对映选择性之间的合理平衡。报道了用于制备更具立体选择性的催化剂的钛-salan 催化剂的改进合成。
• Organocatalytic Asymmetric Synthesis of Sulfoxides from Sulfenic Acid Anions Mediated by a <i>Cinchona</i>-Derived Phase-Transfer Reagent
  作者：Fabien Gelat、Jayadevan Jayashankaran、Jean-François Lohier、Annie-Claude Gaumont、Stéphane Perrio

  DOI：10.1021/ol2010962

  日期：2011.6.17

  Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.

  本文描述了有关手性亚砜在手性相转移催化剂介导的亚磺酸盐与烷基卤化物的不对称烷基化的基础上获得手性亚砜的新颖方法的初步结果。作为代表性的例子，ö -anisyl甲基亚砜，96％收率和58％对映体过量使用商业金鸡尼丁衍生物制备2A。
• Efficient HPLC enantiomer separation using a pillared homochiral metal–organic framework as a novel chiral stationary phase
  作者：Koichi Tanaka、Naoki Hotta、Shohei Nagase、Kenji Yoza

  DOI：10.1039/c6nj00090h

  日期：——

  HPLC enantioseparation of various racemates using novel pillared homochiral MOF–silica composite as chiral stationary phase has been successfully demonstrated.

  使用新型柱状纯手性 MOF-二氧化硅复合物作为手性固定相对各种外消旋物进行 HPLC 对映体分离已被成功证明。
• Investigations on the Iron-Catalyzed Asymmetric Sulfide Oxidation
  作者：Julien Legros、Carsten Bolm

  DOI：10.1002/chem.200400857

  日期：2005.2.4

  The development of an enantioselective sulfide oxidation involving a chiral iron catalyst and aqueous hydrogen peroxide as oxidant is described. In the presence of a simple carboxylic acid, or a carboxylate salt, the reaction affords sulfoxides with remarkable enantioselectivities (up to 96 % ee) in moderate to good yields. The influence of the structure of the additive on the reaction outcome is reported

  描述了涉及手性铁催化剂和过氧化氢水溶液作为氧化剂的对映选择性硫化物氧化的发展。在简单的羧酸或羧酸盐的存在下，该反应以中等至良好的产率提供了具有显着对映选择性（高达96％ee）的亚砜。报道了添加剂的结构对反应结果的影响。在亚砜到砜的氧化过程中，会发生动力学拆分（s = 4.8），但在整个对映选择性过程中，其作用微不足道。此外，已经发现产物的ee与催化剂的ee之间存在正非线性关系。基于这些观察，提出了可能的催化剂结构。
• Efficient soluble polymer-supported tartrate/Ti catalyst for asymmetric oxidation of prochiral sulfides
  作者：Jinshan Gao、Hongchao Guo、Shangzhong Liu、Min Wang

  DOI：10.1016/j.tetlet.2007.09.169

  日期：2007.11

  A group of soluble polymer-supported chiral tartrate ligands was prepared by liquid-phase synthesis with ligand diversity strategy. Moderate to excellent chemical yields and enantiomeric excesses were obtained by using soluble polymer-supported tartrate ester in asymmetric oxidation of prochiral sulfides using Ti(O-i-Pr)4/cumyl hydroperoxide, and the workup was greatly simplified. The influence of

  采用配体多样性策略，通过液相合成制备了一组可溶性聚合物负载的手性酒石酸盐配体。在Ti（O- i- Pr）4 /枯基氢过氧化物的前手性硫化物的不对称氧化中，通过使用可溶性聚合物负载的酒石酸酯来获得中等至优异的化学收率和对映体过量，大大简化了后处理。公开了手性酒石酸酯配体中取代基对反应对映选择性的影响。