(R)-2-(fluoromethyl)-2-(<(R)-(4-methylphenyl)sulfinyl>methyl)oxirane | 144864-60-8

• 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: (R)-2-(fluoromethyl)-2-(<(R)-(4-methylphenyl)sulfinyl>methyl)oxirane
• 英文别名: (2R,Rs)-2-(fluoromethyl)-2-<(4-methylphenylsulphinyl)methyl>oxirane
• CAS: 144864-60-8
• 化学式: C₁₁H₁₃FO₂S
• 分子量: 228.287
• InChiKey: BLJFABJHMJDWMH-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (+)-(R)-1-fluoro-3-<(4-methylphenyl)sulfinyl>-2-propanone 以 乙醚 为溶剂， 反应 4.0h， 生成 (R)-2-(fluoromethyl)-2-(<(R)-(4-methylphenyl)sulfinyl>methyl)oxirane 、 1-[(R)-[(Z)-3-fluoro-2-methoxyprop-1-enyl]sulfinyl]-4-methylbenzene
  参考文献：
  名称：

  Synthesis of fluorinated chirons: Stereoselective oxirane formation by reaction of diazomethane on 1-fluoro-3-arylsulfinyl-2-propanone and ring opening by selected nucleophiles

  摘要：

  (R)-1-fluoro-3-[(4-methylphenyl)sulfinyl]-2-propanone (1) reacts with diazomethane affording (S)-2-(fluoromethyl)-2- {[(R)-(4-methylphenyl)sulfinyl]methyl}oxirane (2) as the main product. The influence of reaction conditions (solvent, temperature) on the chemo- and stereoselectivity has been studied. Several elaborations of 2, including reactions on the chiral auxiliary and opening of the oxirane ring by carbon, nitrogen oxygen, phosphorus and halogen nucleophiles, are described. Full structural elucidation of the products is provided

  DOI：

  10.1016/0040-4020(95)00430-g

文献信息

• A new versatile fluorinated C4 chiron
  作者：Alberto Arnone、Pierfrancesco Bravo、Giancarlo Cavicchio、Massimo Frigerio、Valeria Marchetti、Fiorenza Viani、Carmela Zappalà

  DOI：10.1016/s0040-4039(00)61160-7

  日期：1992.9

  Optically pure 2-(fluoromethyl)-2-[(4-methylphenylsulphinyl)methyl]oxirane has been obtained in good yield and with high d.e. by reacting diazomethane with optically pure 1-fluoro-3-(4-methylphenylsulphinyl)propan-2-one. Regio- and stereo-selective openings of oxirane ring performed with selected nucleophiles afforded several useful derivatives.

  通过使重氮甲烷与光学纯的1-氟-3-（4-甲基苯基亚磺酰基）丙烷-2-反应，以高收率和高脱除率获得光学纯的2-（氟甲基）-2-[（4-甲基苯基亚磺酰基）甲基]环氧乙烷。一。用选定的亲核试剂进行的环氧乙烷环的区域和立体选择性开环提供了几种有用的衍生物。