(S,S)-(-)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine | 155996-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S,S)-(-)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine
• 英文别名: (E,2S)-N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]-3-methyl-2-methylsulfanylbutan-1-imine
• CAS: 155996-78-4
• 化学式: C₁₂H₂₄N₂OS
• 分子量: 244.401
• InChiKey: KMQLYMDYCPOGSL-ZSEQQEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S,S)-(-)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-(+)-3-methyl-2-methylthio-butanal 、 (R)-(-)-3-methyl-2-methylthio-butanal
  参考文献：
  名称：

  Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones

  摘要：

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.

  DOI：

  10.1016/s0040-4020(01)87015-0
• 作为产物：
  描述：

  (S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine 在 lithium diisopropyl amide 作用下， 反应 8.5h， 生成 (S,S)-(-)-2-methoxymethyl-1-(2-methylthio-3-methyl-1'-butylidenamino)-pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones

  摘要：

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.

  DOI：

  10.1016/s0040-4020(01)87015-0

文献信息

• Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones
  作者：Dieter Enders、Thomas Schäfer、Olivier Piva、Andrea Zamponi

  DOI：10.1016/s0040-4020(01)87015-0

  日期：1994.3

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.