Z-Ala-ψ[(C2N2O)SH] | 1360470-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-Ala-ψ[(C2N2O)SH]
• 英文别名: Carbamic acid, N-[(1S)-1-(4,5-dihydro-5-thioxo-1,3,4-oxadiazol-2-yl)ethyl]-, phenylmethyl ester；benzyl N-[(1S)-1-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)ethyl]carbamate
• CAS: 1360470-81-0
• 化学式: C₁₂H₁₃N₃O₃S
• 分子量: 279.32
• InChiKey: DZXSNZGQVRQIKT-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Z-Ala-ψ[(C2N2O)SH] 、 (S)-2-(N-fluorenylmethoxycarbonylamino)-3-phenyl-iodopropane 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以79%的产率得到benzyl N-[(1S)-1-[5-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropyl]sulfanyl-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
• 作为产物：
  描述：

  二硫化碳 、 Z-Ala-NH-NH2 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以70%的产率得到Z-Ala-ψ[(C2N2O)SH]
  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