(-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-(N-benzyloxycarbonyl)aminopropyl-(1-naphthyl)sulfoxide | 1020850-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-(N-benzyloxycarbonyl)aminopropyl-(1-naphthyl)sulfoxide
• 英文别名: (-)-(2S,S_s)-3,3-difluoro-3-phenyl-2-(N-benzyloxycarbonyl)aminopropyl-(1-naphthyl)sulfoxide
• CAS: 1020850-64-9
• 化学式: C₂₇H₂₃F₂NO₃S
• 分子量: 479.547
• InChiKey: YRXFQOIFOYXHQN-GZGVDWRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-(N-benzyloxycarbonyl)aminopropyl-(1-naphthyl)sulfoxide 在 2,4,6-三甲基吡啶 、 四氯化钛 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.33h， 生成 (4R)-4-(phenyldifluoromethyl)-N-(2S,3S)-(3-hydroxy-2,4-dimethyl-pentanoyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of a new fluorinated oxazolidinone and its reactivity as a chiral auxiliary in Aldol reactions

  摘要：

  A new enantiomerically pure fluorinated oxazolidinone has been prepared from a fluorinated imidoyl chloride and an optically pure sulfoxide. The diastereoselective reduction of the beta-iminosulfoxide thus formed followed by elimination of the sulfoxide and cyclization of the created aminoalcohol furnishes the desired product. The fluorinated oxazolidinone was subsequently used as a chiral auxiliary in Aldol reactions. We also found that the selective formation of the syn-Evans and syn-non-Evans diastereoisomer can be controlled by adjusting the Lewis acid/base ratio. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.03.001
• 作为产物：
  描述：

  (S)-(-)-methyl 1-naphthyl sulfoxide 在 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 水 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 5.0h， 生成 (-)-(2S,Ss)-3,3-difluoro-3-phenyl-2-(N-benzyloxycarbonyl)aminopropyl-(1-naphthyl)sulfoxide
  参考文献：
  名称：

  Synthesis of a new fluorinated oxazolidinone and its reactivity as a chiral auxiliary in Aldol reactions

  摘要：

  A new enantiomerically pure fluorinated oxazolidinone has been prepared from a fluorinated imidoyl chloride and an optically pure sulfoxide. The diastereoselective reduction of the beta-iminosulfoxide thus formed followed by elimination of the sulfoxide and cyclization of the created aminoalcohol furnishes the desired product. The fluorinated oxazolidinone was subsequently used as a chiral auxiliary in Aldol reactions. We also found that the selective formation of the syn-Evans and syn-non-Evans diastereoisomer can be controlled by adjusting the Lewis acid/base ratio. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.03.001