(R)-S-2-hydroxyphenyl S-1-methylethyl sulfoximine | 177944-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-S-2-hydroxyphenyl S-1-methylethyl sulfoximine
• CAS: 177944-25-1
• 化学式: C₉H₁₃NO₂S
• 分子量: 199.274
• InChiKey: HTFVPQWTLDDQLE-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.15
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-S-2-hydroxyphenyl S-1-methylethyl sulfoximine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.67h， 生成 (R)-S-2-hydroxyphenyl S-1,1-dimethylethyl 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)-S-(2-methoxyphenyl)-S-methylsulfoximine 在 正丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (R)-S-2-hydroxyphenyl S-1-methylethyl 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

文献信息

• 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.