methyl (S)-N-(2-methylpropanethioyl)norprolinate | 445396-38-3

• 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: methyl (S)-N-(2-methylpropanethioyl)norprolinate
• CAS: 445396-38-3
• 化学式: C₉H₁₅NO₂S
• 分子量: 201.29
• InChiKey: MEVBSWXDLBUYLE-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-N-(2-methylpropanethioyl)norprolinate 在 N,N-二甲基甲酰胺 、 三乙烯二胺 、 sodium azide 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 49.33h， 生成 (S)-1-(1,1-Diazido-2-methyl-propyl)-azetidine-2-carboxylic acid methyl ester 、 (S)-1-[1-Azido-2-methyl-prop-(Z)-ylidene]-2-methoxycarbonyl-azetidinium; GENERIC INORGANIC ANION
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z
• 作为产物：
  描述：

  methyl (S)-azetidine-2-carboxylate 在 劳森试剂 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl (S)-N-(2-methylpropanethioyl)norprolinate
  参考文献：
  名称：

  Synthesis and Use of 2H-Azirin-3-amines as Dipeptide Synthons

  摘要：

  The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx = alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

  DOI：

  10.1002/1522-2675(200203)85:3<885::aid-hlca885>3.0.co;2-z