tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate | 143327-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate
• CAS: 143327-92-8；143327-93-9
• 化学式: C₁₆H₂₇NO₄
• 分子量: 297.395
• InChiKey: PJUDEPIDBYWBKK-ZNFYDKSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 4-[(E,3S)-3-amino-4-methylpent-1-enyl]oxan-2-one
  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：

  5,6-dihydro-pyran-2-one 、 2-甲基-2-丙基[(3S)-4-甲基-1-戊炔-3-基]氨基甲酸酯 在 nickel(II) iodide Schwartz's reagent 作用下， 生成 tert-butyl N-[(E,3S)-4-methyl-1-(2-oxooxan-4-yl)pent-1-en-3-yl]carbamate
  参考文献：
  名称：

  手性炔丙基胺的制备与反应

  摘要：

  将手性氨基醛（1）暴露于重氮膦酸二甲酯（4）可获得高光学纯度的炔丙基胺（2）。这些中间体的扩链很容易通过乙炔部分的加氢锆化和随后的Ni（II）催化的Michael加成到各种Michael受体上而实现。

  DOI：

  10.1016/0040-4039(92)80006-6

文献信息

• Preparation and reactions of chiral propargylic amines
  作者：James R. Hauske、Peter Dorff、Susan Julin、Gary Martinelli、Jacqueline Bussolari

  DOI：10.1016/0040-4039(92)80006-6

  日期：1992.6

  Exposure of chiral amino aldehydes (1) to dimethyl diazophosphonate (4) affords propargylic amines (2) of high optical purity. Chain extension of these intermediates is readily accomplished via hydrozirconation of the acetylene moiety and subsequent Ni(II) catalyzed Michael addition to a variety of Michael acceptors.

  将手性氨基醛（1）暴露于重氮膦酸二甲酯（4）可获得高光学纯度的炔丙基胺（2）。这些中间体的扩链很容易通过乙炔部分的加氢锆化和随后的Ni（II）催化的Michael加成到各种Michael受体上而实现。
• 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.