N-tert-butylthiomethylproline S-(-)-methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butylthiomethylproline S-(-)-methyl ester
• 英文别名: Methyl 1-(tert-butylthiomethyl-pyrrolidine-2-carboxylate；methyl (2S)-1-(tert-butylsulfanylmethyl)pyrrolidine-2-carboxylate
• 化学式: C₁₁H₂₁NO₂S
• 分子量: 231.359
• InChiKey: ATUQBALEQWWITM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基硫醇 、 N-tert-butylthiomethylproline S-(-)-methyl ester 以74%的产率得到N-methyl-N-tert-butylthiomethyl aspartic acid dimethyl ester
  参考文献：
  名称：

  Mass spectrometry of organic compounds of the group V Elements: VI—A new type of amine fragmentation under electron impact

  摘要：

  AbstractA new type of amine fragmentation under electron impact is elucidated for proline, sarcosine and aspartic acid derivatives and aminomethylphosphines of the general formula R2NCH2X. Ordinary α‐cleavage affording the \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm R}_2 \mathop {\rm N}\limits^{\rm + } {\rm = CH}_{\rm 2} $\end{document} ion is suppressed by elimination of a neutral HX particle and [M ‐ HX]+ ion formation, or M‐HX neutral particle ejection and generation of an [HX]+ ion from [M]+˙. Such fragmentation is ensured by the presence of an α‐heteroatom (N, O, P, S) in one substituent (X) and a CO2R type delocalizing group in the α‐position of the other substituent (R2N).

  DOI：

  10.1002/oms.1210150804
• 作为产物：
  描述：

  甲基1-(甲氧基甲基)-L-脯氨酸酯 、 叔丁基硫醇 反应 12.0h， 以52%的产率得到N-tert-butylthiomethylproline S-(-)-methyl ester
  参考文献：
  名称：

  Mass spectrometry of organic compounds of the group V Elements: VI—A new type of amine fragmentation under electron impact

  摘要：

  AbstractA new type of amine fragmentation under electron impact is elucidated for proline, sarcosine and aspartic acid derivatives and aminomethylphosphines of the general formula R2NCH2X. Ordinary α‐cleavage affording the \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm R}_2 \mathop {\rm N}\limits^{\rm + } {\rm = CH}_{\rm 2} $\end{document} ion is suppressed by elimination of a neutral HX particle and [M ‐ HX]+ ion formation, or M‐HX neutral particle ejection and generation of an [HX]+ ion from [M]+˙. Such fragmentation is ensured by the presence of an α‐heteroatom (N, O, P, S) in one substituent (X) and a CO2R type delocalizing group in the α‐position of the other substituent (R2N).

  DOI：

  10.1002/oms.1210150804

文献信息

• Mass spectrometry of organic compounds of the group V Elements: VI—A new type of amine fragmentation under electron impact
  作者：R. G. Kostyanovsky、V. N. Voznesensky、G. K. Kadorkina、Yu. I. El'natanov

  DOI：10.1002/oms.1210150804

  日期：1980.8

  AbstractA new type of amine fragmentation under electron impact is elucidated for proline, sarcosine and aspartic acid derivatives and aminomethylphosphines of the general formula R2NCH2X. Ordinary α‐cleavage affording the \documentclassarticle}\pagestyleempty}\begindocument}$ \rm R}_2 \mathop \rm N}\limits^\rm + } \rm = CH}_\rm 2} $\enddocument} ion is suppressed by elimination of a neutral HX particle and [M ‐ HX]+ ion formation, or M‐HX neutral particle ejection and generation of an [HX]+ ion from [M]+˙. Such fragmentation is ensured by the presence of an α‐heteroatom (N, O, P, S) in one substituent (X) and a CO2R type delocalizing group in the α‐position of the other substituent (R2N).