tert-butyl [(1S)-1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl]carbamate | 1173685-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl [(1S)-1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl]carbamate
• 英文别名: tert-butyl N-[(1S)-1-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)ethyl]carbamate
• CAS: 1173685-53-4
• 化学式: C₉H₁₅N₃O₃S
• mdl: MFCD03848255
• 分子量: 245.302
• InChiKey: YXKPNCFZPSYTBZ-YFKPBYRVSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

反应信息

• 作为反应物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 、 tert-butyl [(1S)-1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl]carbamate 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.58h， 以76%的产率得到
  参考文献：
  名称：

  A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics

  摘要：

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.093
• 作为产物：
  描述：

  二硫化碳 、 N-tert-butoxycarbonyl-L-alanine hydrazide 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 tert-butyl [(1S)-1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl]carbamate
  参考文献：
  名称：

  A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics

  摘要：

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.093