(S)-2-{(S)-3-Phenyl-2-[((S)-piperidine-2-carbonyl)-amino]-propionylamino}-hex-5-enoic acid tert-butyl ester | 1027960-09-3

• 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: (S)-2-{(S)-3-Phenyl-2-[((S)-piperidine-2-carbonyl)-amino]-propionylamino}-hex-5-enoic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[[(2S)-3-phenyl-2-[[(2S)-piperidine-2-carbonyl]amino]propanoyl]amino]hex-5-enoate
• CAS: 1027960-09-3
• 化学式: C₂₅H₃₇N₃O₄
• 分子量: 443.586
• InChiKey: LJFULQOPJVHNOH-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-溴-3‘-甲氧基苯乙酮 、 (S)-2-{(S)-3-Phenyl-2-[((S)-piperidine-2-carbonyl)-amino]-propionylamino}-hex-5-enoic acid tert-butyl ester 在 potassium fluoride on Celite 作用下， 以 乙腈 为溶剂， 以56%的产率得到(S)-2-[(S)-2-({(S)-1-[2-(3-Methoxy-phenyl)-2-oxo-ethyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-hex-5-enoic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of novel FKBP inhibitors

  摘要：

  Small molecule FKBP inhibitors were prepared with inhibitory activity ranging from micromolar to nanomolar. The design of these inhibitors derives from a structural analysis of the substrates for FKBP and cyclophilin. As a consequence of this analysis two key observations were made, namely: (1) amino ketone moieties are suitable as FKBP recognition elements at the P1-P1' site and (2) the P3'-P4' site will accept a trans-olefin as a suitable mimetic of a peptide moiety. The preparation of these non-peptide inhibitors is readily accomplished by a protocol which includes the synthesis of chiral propargylic amines and their subsequent conversion into vinyl zirconium reagents.

  DOI：

  10.1021/jm00101a005
• 作为产物：
  描述：

  tert-butyl (2S)-2-aminohex-5-enoate 在 palladium dihydroxide 、 氢气 、 1-羟基苯并三唑 、 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， 20.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 (S)-2-{(S)-3-Phenyl-2-[((S)-piperidine-2-carbonyl)-amino]-propionylamino}-hex-5-enoic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of novel FKBP inhibitors

  摘要：

  Small molecule FKBP inhibitors were prepared with inhibitory activity ranging from micromolar to nanomolar. The design of these inhibitors derives from a structural analysis of the substrates for FKBP and cyclophilin. As a consequence of this analysis two key observations were made, namely: (1) amino ketone moieties are suitable as FKBP recognition elements at the P1-P1' site and (2) the P3'-P4' site will accept a trans-olefin as a suitable mimetic of a peptide moiety. The preparation of these non-peptide inhibitors is readily accomplished by a protocol which includes the synthesis of chiral propargylic amines and their subsequent conversion into vinyl zirconium reagents.

  DOI：

  10.1021/jm00101a005