(R)-(+)-2-<(1,1-dimethylethyl)sulfinylmethyl>pyridine | 132065-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-(+)-2-<(1,1-dimethylethyl)sulfinylmethyl>pyridine
• 英文别名: 2-[[(R)-tert-butylsulfinyl]methyl]pyridine
• CAS: 132065-19-1
• 化学式: C₁₀H₁₅NOS
• 分子量: 197.301
• InChiKey: FRBYHQFIEOMEOV-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [2]pyridyl-methyl magnesium (1+); chloride 、 2,2-diphenyl-1,2-dihydroxypropyl 2-O-tert-butylsulfinate 以 乙醚 为溶剂， 反应 0.5h， 生成 (R)-(+)-2-<(1,1-dimethylethyl)sulfinylmethyl>pyridine
  参考文献：
  名称：

  A general route to enantiomerically pure sulfoxides from a chiral sulfite

  摘要：

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.

  DOI：

  10.1021/jo00021a008

文献信息

• Synthesis of new optically active sulfoxides with chelating properties
  作者：Kai - U. Baldenius、Henri B. Kagan

  DOI：10.1016/0957-4166(90)80010-v

  日期：1990.1

  2-pyridinylmethyl sulfoxides and β-imino sulfoxides was sought. The latter were obtained in tautomeric mixtures with their enamines by condensation of optically active β-keto sulfoxides with primary amines. 2-Pyridinylmethyl sulfoxides were synthesized by sulfinate substitution. Titanium catalysed oxidation gave good results for the synthesis of (+)-8-(methylsulfinyl)quinoline from the corresponding

  寻求获得对映体纯的2-吡啶基甲基亚砜和β-亚氨基亚砜。后者是通过将旋光性β-酮亚砜与伯胺缩合而与它们的烯胺以互变异构体混合物的形式获得的。通过亚磺酸酯取代合成2-吡啶基甲基亚砜。钛催化的氧化为由相应的硫化物合成（+）-8-（甲基亚磺酰基）喹啉提供了良好的结果。
• Methods of Preparing Sulfinamides and Sulfoxides
  申请人：Senanayake Hugh Chris

  公开号：US20070293682A1

  公开（公告）日：2007-12-20

  This invention encompasses novel methods of preparing sulfinamides and sulfoxides, particularly stereomerically pure sulfinamides and sulfoxides. The invention further encompasses novel compounds from which sulfinamides and sulfoxides can be prepared.

  本发明涵盖了制备磺酰胺和磺醇的新方法，特别是立体异构纯的磺酰胺和磺醇。该发明还涵盖了可以制备磺酰胺和磺醇的新化合物。
• US7256297B2
  申请人：——

  公开号：US7256297B2

  公开（公告）日：2007-08-14