(-)-(2S,S_S)-3,3-difluoro-N-(p-methoxyphenyl)-2-amino-5-hexenyl-1-(1-naphtyl)sulfoxide | 364049-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-(2S,S_S)-3,3-difluoro-N-(p-methoxyphenyl)-2-amino-5-hexenyl-1-(1-naphtyl)sulfoxide
• 英文别名: N-[(2S)-3,3-difluoro-1-[(S)-naphthalen-1-ylsulfinyl]hex-5-en-2-yl]-4-methoxyaniline
• CAS: 364049-23-0
• 化学式: C₂₃H₂₃F₂NO₂S
• 分子量: 415.504
• InChiKey: NEBREUVDVGIURC-MNNSJKJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(2S,S_S)-3,3-difluoro-N-(p-methoxyphenyl)-2-amino-5-hexenyl-1-(1-naphtyl)sulfoxide 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 9.83h， 生成 (-)-(1R)-2,2-difluoro-1-methyl-O-benzoyl-4-pentyl(benzyloxycarbonyl)amine
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q
• 作为产物：
  描述：

  (S)-(-)-methyl 1-naphthyl sulfoxide 在 tetrabutylammonium borohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 (-)-(2S,S_S)-3,3-difluoro-N-(p-methoxyphenyl)-2-amino-5-hexenyl-1-(1-naphtyl)sulfoxide
  参考文献：
  名称：

  Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol

  摘要：

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.

  DOI：

  10.1021/ol016087q

文献信息

• Enantioselective Synthesis of Fluorinated α-Amino Acids and Derivatives in Combination with Ring-Closing Metathesis:  Intramolecular π-Stacking Interactions as a Source of Stereocontrol
  作者：Santos Fustero、Antonio Navarro、Belén Pina、Juan García Soler、Ana Bartolomé,、Amparo Asensio、Antonio Simón、Pierfrancesco Bravo、Giovanni Fronza、Alessandro Volonterio、Matteo Zanda

  DOI：10.1021/ol016087q

  日期：2001.8.1

  [GRAPHICS]Hydride reduction of C=N bonds stereocontrolled by intramolecular m-stacking interactions of 1-naphthylsulfinyl and N-aryl groups, nonoxidative Pummerer rearrangement, and ring-closing metathesis are efficiently combined in a highly stereoselective entry to enantiomerically pure cyclic and acyclic fluorinated beta -amino alcohols and alpha -amino acid derivatives, respectively.