Benzoic acid (E)-(S)-4-tert-butoxycarbonylamino-5-methyl-hex-2-enyl ester | 145037-58-7

• 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: Benzoic acid (E)-(S)-4-tert-butoxycarbonylamino-5-methyl-hex-2-enyl ester
• 英文别名: [(E,4S)-5-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]hex-2-enyl] benzoate
• CAS: 145037-58-7
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: SQDPFCYBUDHVIP-ONOODXEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid (E)-(S)-4-tert-butoxycarbonylamino-5-methyl-hex-2-enyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 Benzoic acid (E)-(S)-4-amino-5-methyl-hex-2-enyl 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：

  苯甲酰氯 、 tert-butyl (S,E)-(6-hydroxy-2-methylhex-4-en-3-yl)carbamate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 Benzoic acid (E)-(S)-4-tert-butoxycarbonylamino-5-methyl-hex-2-enyl 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

文献信息

• Design and synthesis of novel FKBP inhibitors
  作者：James R. Hauske、Peter Dorff、Susan Julin、Joseph DiBrino、Robin Spencer、Rebecca Williams

  DOI：10.1021/jm00101a005

  日期：1992.11

  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.