(S)-tert-butyl 2-(formamidomethyl)pyrrolidine-1-carboxylate | 1245908-77-3

• 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)-tert-butyl 2-(formamidomethyl)pyrrolidine-1-carboxylate
• 英文别名: Boc-Pro-ψ[CH2NHCHO]；tert-Butyl (S)-2-(formamidomethyl)pyrrolidine-1-carboxylate；tert-butyl (2S)-2-(formamidomethyl)pyrrolidine-1-carboxylate
• CAS: 1245908-77-3
• 化学式: C₁₁H₂₀N₂O₃
• 分子量: 228.291
• InChiKey: JXMNLOJYGIKZEM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-(formamidomethyl)pyrrolidine-1-carboxylate 在 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-(S)-isocyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082
• 作为产物：
  描述：

  甲酸 、 S-叔丁氧羰基-2-(氨基乙基)吡咯烷 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到(S)-tert-butyl 2-(formamidomethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082