(+)-(SS)-{3,3-二氟-3-苯基-2-[N-(对甲氧基苯基)亚氨基]丙基}-(1-萘基)亚砜 | 1020850-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (+)-(SS)-{3,3-二氟-3-苯基-2-[N-(对甲氧基苯基)亚氨基]丙基}-(1-萘基)亚砜
• 英文名称: (+)-(Ss)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide
• 英文别名: (+)-(S_s)-{3,3-difluoro-3-phenyl-2-[N-(p-methoxyphenyl)imino]propyl}-(1-naphthyl)sulfoxide
• CAS: 1020850-62-7
• 化学式: C₂₆H₂₁F₂NO₂S
• 分子量: 449.521
• InChiKey: QRQFPEAODZGALE-TYINEUDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-(SS)-{3,3-二氟-3-苯基-2-[N-(对甲氧基苯基)亚氨基]丙基}-(1-萘基)亚砜 在 2,4,6-三甲基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 水 、 四氯化钛 、 sodium hydride 、 potassium carbonate 、 三氟乙酸酐 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.41h， 生成 (4R)-4-(phenyldifluoromethyl)-N-(2R,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 、 2,2-difluoro-N-(4-methoxyphenyl)-2-phenylacetimidoyl chloride 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(+)-(SS)-{3,3-二氟-3-苯基-2-[N-(对甲氧基苯基)亚氨基]丙基}-(1-萘基)亚砜
  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