(3S,5S,2'S)-5-(N-(n-butoxycarbonyl)pyrrolidin-2'-yl)-6(E)-(bromomethylene)-3-isopropyl-4-oxatetrahydro-2-pyranone | 132127-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3S,5S,2'S)-5-(N-(n-butoxycarbonyl)pyrrolidin-2'-yl)-6(E)-(bromomethylene)-3-isopropyl-4-oxatetrahydro-2-pyranone
• 英文别名: (3S,5S,2'S)-5-[N-(n-butoxycarbonyl)pyrrolidin-2'-yl]-6(E)-(bromomethylene)-3-isopropyl-4-oxatetrahydro-2-pyranone；butyl (2S)-2-[(2S,3E,6S)-3-(bromomethylidene)-5-oxo-6-propan-2-yl-1,4-dioxan-2-yl]pyrrolidine-1-carboxylate
• CAS: 132127-37-8
• 化学式: C₁₇H₂₆BrNO₅
• 分子量: 404.301
• InChiKey: WVKIAZOUUZRCNI-KHXOAPOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,4R,2'S)-4-(N-(n-butyloxycarbonyl)pyrrolidin-2'yl)-2-isopropyl-3-oxahex-5-ynoic acid 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydrogencarbonate 作用下， 生成 (3S,5S,2'S)-5-(N-(n-butoxycarbonyl)pyrrolidin-2'-yl)-6(E)-(bromomethylene)-3-isopropyl-4-oxatetrahydro-2-pyranone
  参考文献：
  名称：

  Synthesis of proline-valine pseudodipeptide enol lactones, serine protease inhibitors

  摘要：

  Pseudodipeptides of proline-valine that incorporate protio or halo enol lactone moieties have been synthesized from common acetylenic acid precursors; in each case, two diasteromers were prepared in enantiomerically pure form. The preparation began with isomeric propargylic alcohols derived from L-prolinal, which are further elaborated into the methyleneoxy valine pseudodipeptide analogues via an oxalactam intermediate. Stereochemical assignments were made by comparisons of nuclear Overhauser enhancement factors. The pseudodipeptide acetylenic acids could by cyclized to the protio enol lactones by mercuric salts and could be elaborated to tetrapeptide analogues either before or after cyclization. The relative stability of the two diastereomeric enol lactone systems toward intramolecular acyl transfer could be rationalized by molecular mechanics energy calculations on ground-state and tetrahedral intermediates believed to be involved in the reaction. While the halo enol lactones derived from the pseudotetrapeptides proved to be very unstable, they could be prepared from the n-butyl carbamate derivatives of the dipeptide. An evaluation of these protio and halo enol lactone systems as inhibitors of serine proteases will be discussed elsewhere.

  DOI：

  10.1021/jo00008a011

文献信息

• REED, PETER E.;KATZENELLENBOGEN, JOHN A., J. ORG. CHEM., 56,(1991) N, C. 2624-2634
  作者：REED, PETER E.、KATZENELLENBOGEN, JOHN A.

  DOI：——

  日期：——