(R)-S-(2-methoxynaphth-1-yl)-S-methyl sulfoximide | 177944-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-S-(2-methoxynaphth-1-yl)-S-methyl sulfoximide
• 英文别名: imino-(2-methoxynaphthalen-1-yl)-methyl-oxo-λ6-sulfane
• CAS: 177944-31-9
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: YZPKWSHTIIFXJT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(+)-(R) methyl 2-methoxy-1-naphthyl sulfoxide	155135-09-4	C12H12O2S	220.292

反应信息

• 作为反应物：
  描述：

  (R)-S-(2-methoxynaphth-1-yl)-S-methyl sulfoximide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(R)-S-2-hydroxynaphthyl S-methyl sulfoximine
  参考文献：
  名称：

  Sulfoximine--Titanium Reagents in Enantioselective Trimethylsilylcyanations of Aldehydes.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.50-0305
• 作为产物：
  描述：

  (+)-(R) methyl 2-methoxy-1-naphthyl sulfoxide 在 2,4,6-三甲基苯磺酰羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到(R)-S-(2-methoxynaphth-1-yl)-S-methyl sulfoximide
  参考文献：
  名称：

  Sulfoximine--Titanium Reagents in Enantioselective Trimethylsilylcyanations of Aldehydes.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.50-0305

文献信息

• 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。
• Ethylene-Bridged Bissulfoximines in Copper-Catalyzed Enantioselective Hetero-Diels--Alder Reactions
  作者：Carsten Bolm、Marinella Verrucci、Oliver Simic、Christian P. R. Hackenberger

  DOI：10.1002/adsc.200505104

  日期：2005.10

  Ethylene-bridged bissulfoximines were applied as chiral ligands in copper-catalyzed enantioselective hetero-Diels–Alder reactions. After optimization of the reaction conditions, products with up to 99% ee were obtained.

  在铜催化的对映选择性杂-Diels-Alder反应中，乙烯桥联的双硫代亚砜被用作手性配体。在优化反应条件后，获得具有高达99％ee的产物。
• 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.