(2S)-2-[[cyclopentyl-(4-methylphenyl)-oxo-lambda6-sulfanylidene]amino]-3-methylbutan-1-ol | 145624-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[[cyclopentyl-(4-methylphenyl)-oxo-lambda6-sulfanylidene]amino]-3-methylbutan-1-ol
• 英文别名: (2S)-2-[[cyclopentyl-(4-methylphenyl)-oxo-λ6-sulfanylidene]amino]-3-methylbutan-1-ol
• CAS: 145624-67-5
• 化学式: C₁₇H₂₇NO₂S
• 分子量: 309.473
• InChiKey: WMYKGGNMQXAAJW-UTKZUKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲基苯基亚硫酰氯 在 potassium fluoride 、 18-冠醚-6 、 二甲基十二/十四烷基叔胺 、 次氯酸叔丁酯 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 乙腈 为溶剂， 反应 25.58h， 生成 (2S)-2-[[cyclopentyl-(4-methylphenyl)-oxo-lambda6-sulfanylidene]amino]-3-methylbutan-1-ol
  参考文献：
  名称：

  One-pot synthesis of (S)-4-isopropyl-2-p-toluene-4,5-dihydro-[1.2λ6,3]oxathiazole 2-Oxides: Efficient precursors of optically active sulfoximines

  摘要：

  The title compounds were prepared from p-toluenesulfinyl chloride and (S)-O-trimethylsilyl valinol without isolation of intermediates. Key step in the synthesis is the fluoride-induced cyclisation of sulfonimidoyl chlorides yielding the crystalline sulfonimidates 4 and 5 as a mixture of enantiomerically pure diastereomers which were easily separable by column chromatography or just simple crystallisation. Their reactions with either organolithium or Grignard reagents offer a convenient entry to enantiomerically pure sulfoximines in high yields.

  DOI：

  10.1016/s0040-4039(00)60906-1

文献信息

• One-pot synthesis of (S)-4-isopropyl-2-p-toluene-4,5-dihydro-[1.2λ6,3]oxathiazole 2-Oxides: Efficient precursors of optically active sulfoximines
  作者：Michael Reggelin、Heinz Weinberger

  DOI：10.1016/s0040-4039(00)60906-1

  日期：1992.11

  The title compounds were prepared from p-toluenesulfinyl chloride and (S)-O-trimethylsilyl valinol without isolation of intermediates. Key step in the synthesis is the fluoride-induced cyclisation of sulfonimidoyl chlorides yielding the crystalline sulfonimidates 4 and 5 as a mixture of enantiomerically pure diastereomers which were easily separable by column chromatography or just simple crystallisation. Their reactions with either organolithium or Grignard reagents offer a convenient entry to enantiomerically pure sulfoximines in high yields.