(R)-S-(2-methoxyphenyl)-S-methylsulfoximine | 177944-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-S-(2-methoxyphenyl)-S-methylsulfoximine
• 英文别名: Imino-(2-methoxyphenyl)-methyl-oxo-lambda6-sulfane；imino-(2-methoxyphenyl)-methyl-oxo-λ6-sulfane
• CAS: 177944-29-5
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: BSTGEFDBACVVDH-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-S-(2-methoxyphenyl)-S-methylsulfoximine 在 copper(l) iodide 、 cesium acetate 、 铁粉 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 (R)-N-[2-(2,4,6-trimethylbenzylamino)phenyl]-S-(2-methoxyphenyl)-S-methylsulfoximine
  参考文献：
  名称：

  C1-对称氨基亚砜亚胺作为铜催化羰基-烯反应中的配体

  摘要：

  高度模块化的 C 1 -对称氨基亚砜亚胺被制备并用作铜催化的对映选择性羰基-烯反应中的手性配体。优化的系统催化丙酮酸和 1,1-二取代烯烃的转化，以中等产率产生具有高对映体过量（高达 91% ee）的相应羟基酯。

  DOI：

  10.1055/s-2005-863737
• 作为产物：
  描述：

  methyl o-methoxyphenyl sulfoxide 在 碘苯二乙酸 、 氨基甲酸铵 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以51%的产率得到(R)-S-(2-methoxyphenyl)-S-methylsulfoximine
  参考文献：
  名称：

  Chiral Analogues of PFI-1 as BET Inhibitors and Their Functional Role in Myeloid Malignancies

  摘要：

  Structural analogues of PFI-1 varying at the sulfur core were prepared, and their activities as BET inhibitors in myeloid cell lines and primary cells from patients with acute myeloid leukemia were studied. Docking calculations followed by molecular dynamics simulations revealed the binding mode of the newly prepared inhibitors, suggesting explanations for the observed high enantiospecificity of the inhibitory activity.

  DOI：

  10.1021/acsmedchemlett.9b00625

文献信息

• Highly Modular Synthesis ofC1-Symmetric Aminosulfoximines and Their Use as Ligands in Copper-Catalyzed Asymmetric Mukaiyama-Aldol Reactions
  作者：Martin Langner、Pauline Rémy、Carsten Bolm

  DOI：10.1002/chem.200500497

  日期：2005.10.21

  The development of C1-symmetric aminosulfoximines, their highly modular synthesis, and their application in enantioselective copper-catalyzed Mukaiyama-type aldol reactions between pyruvates and enolsilanes is described. In this context, the influence of the ligand architecture as well as the optimization of the reaction conditions are discussed. In detail, the dependence of the catalyst efficiency

  描述了C1对称氨基亚砜肟的开发，其高度模块化的合成及其在丙酮酸和烯醇硅烷之间的对映选择性铜催化的Mukaiyama型醛醇缩合反应中的应用。在这种情况下，讨论了配体结构的影响以及反应条件的优化。详细地，报道了催化剂效率对溶剂，金属源和温度的依赖性，并且突出了有趣的加合效应。此外，将介绍基板范围。通过优化的催化剂体系，已经以高收率获得了许多具有季生立体中心的醛醇缩合产物，对映体过量高达99％。
• <i>C</i>₂-Symmetric Bissulfoximines as Ligands in Copper-Catalyzed Enantioselective Diels−Alder Reactions
  作者：Carsten Bolm、Marc Martin、Oliver Simic、Marinella Verrucci

  DOI：10.1021/ol027273e

  日期：2003.2.1

  [reaction: see text] Bissulfoximines have been used as chiral ligands in copper-catalyzed enantioselective Diels-Alder reactions between acryloyl-2-oxazolidinones and cyclopentadiene. After optimizing the ligand structure, the metal source, the counterions, and the solvent, products with up to 93% ee have been obtained.

  [反应：见正文]在铜催化的丙烯酰基-2-恶唑烷酮与环戊二烯之间的对映选择性Diels-Alder反应中，双硫肟酮已被用作手性配体。在优化配体结构，金属源，抗衡离子和溶剂后，可得到ee高达93％的产品。
• A Mild Synthetic Procedure for the Preparation of N-Alkylated Sulfoximines
  作者：Carsten Bolm、Christian P. R. Hackenberger、Oliver Simić、Marinella Verrucci、Dirk Müller、Frank Bienewald

  DOI：10.1055/s-2002-28514

  日期：——

  N-Alkylated sulfoximines have been synthesized in good yields by acylation of NH-sulfoximines followed by carbonyl reduction with complexed boranes. Enantiopure substrates react without racemization, and stereogenic centers originating from the acylating component are retained. If the acylation is performed by DCC coupling, this two-step procedure represents a rare example of a formal N-alkylation of sulfoximines under base-free conditions.

  N-烷基化的磺氧亚胺通过对NH-磺氧亚胺进行酰化，随后用复合硼烷进行羰基还原，成功合成并获得良好产率。手性纯的底物在反应中不会发生消旋化，并且来自酰化组分的立体中心得到保留。如果酰化是通过DCC偶联进行的，这种两步法代表了在无碱条件下磺氧亚胺的正式N-烷基化的一个罕见例子。
• C2-Symmetric Bissulfoximines in Palladium-catalyzed Allylic Alkylations
  作者：Carsten Bolm、Oliver Simić、Marc Martin

  DOI：10.1055/s-2001-18756

  日期：——

  C2-Symmetric bissulfoximines 2 have been used as chiral ligands in palladium-catalyzed asymmetric allylic alkylations. With 2c enantioselectivities of up to 98% ee have been achieved in the reaction of 1,3-diphenylpropenyl acetate with malonates as nucleophiles.

  在钯催化的不对称烯丙基烷基化反应中，C2-对称双磺酰亚胺 2 被用作手性配体。在 1,3-二苯基丙烯乙酸酯与丙二酸盐作为亲核物的反应中，2c 的对映选择性高达 98%ee。
• Sulfoximine--Titanium Reagents in Enantioselective Trimethylsilylcyanations of Aldehydes.
  作者：Carsten Bolm、Peter Müller、Klaus Harms、Kim Simonsen、György Liptay、Katrin Trautwein-Fritz、Joseph Stackhouse、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0305

  日期：——

  Chiral titanium reagents derived from optically active sulfoximines and Ti(O-i-Pr)(4) promote the asymmetric addition of trimethysilyl cyanide to aldehydes affording cyanohydrins in high yields with good enantioselectivities (up to 91% ee). The ligand structure and the reaction conditions have been optimized. With substoichiometric amounts of the sulfoximine-titanium reagent the product is obtained in decreased yield with lower enantiomeric excess. The molecular structures of (R)-S-(2-hydroxyphenyl)-S-methyl sulfoximine [(R)-4a] and (R)-S-(2-hydroxyphenyl)-S-(1,1-dimethylethyl) sulfoximine [(R)-4d] have been determined by X-ray diffraction analysis.