(S)-N-(tert-butyl)alaninamide trifluoroacetate | 1272660-68-0

• 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: (S)-N-(tert-butyl)alaninamide trifluoroacetate
• 英文别名: H-L-Ala-NHtBu TFA
• CAS: 1272660-68-0
• 化学式: C₂HF₃O₂*C₇H₁₆N₂O
• 分子量: 258.241
• InChiKey: BNODJDNSJKWSBQ-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  92.42
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2RS)-2-benzyl-1-benzyloxycarbonyl-2-carboxylazetidine 、 (S)-N-(tert-butyl)alaninamide trifluoroacetate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(2S,1'S)-2-benzyl-1-benzyloxycarbonyl-2-[(1'-tert-butylcarbamoyl)ethyl]carbamoylazetidine
  参考文献：
  名称：

  Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors

  摘要：

  SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by H-1 NMR as a gamma-type reverse turn, seems to have influence on the activity of these molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.052
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-(L)-alanine tert-butylamide 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-N-(tert-butyl)alaninamide trifluoroacetate
  参考文献：
  名称：

  Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors

  摘要：

  SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by H-1 NMR as a gamma-type reverse turn, seems to have influence on the activity of these molecules. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.052