(R)-2-(N-benzyl-N-((1R,2S,3R,4S)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)amino)-N-benzyl-2-phenylacetamide | 1196683-91-6

• 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: (R)-2-(N-benzyl-N-((1R,2S,3R,4S)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)amino)-N-benzyl-2-phenylacetamide
• 英文别名: (2R)-N-benzyl-2-[benzyl-[(1R,2S,3R,4S)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl]amino]-2-phenylacetamide
• CAS: 1196683-91-6
• 化学式: C₂₉H₃₀N₂O₃
• 分子量: 454.569
• InChiKey: LFBANSCLEZGOIH-QLHPUIKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(N-benzyl-N-((1R,2S,3R,4S)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)amino)-N-benzyl-2-phenylacetamide 、 苯硼酸 在 二(氰基苯)二氯化钯 、 1,3-双(二苯基膦)丙烷 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 (2R)-N-benzyl-2-{N-benzyl-N-[(1S,2R,5S,6R)-6-hydroxy-2-(hydroxymethyl)-5-phenyl-3-cyclohexene-1-yl]amino}-2-phenylacetamide
  参考文献：
  名称：

  Identification of Lead Compounds As Antagonists of Protein Bcl-x_L with a Diversity-Oriented Multidisciplinary Approach

  摘要：

  We report on the use of a diversity oriented synthesis (DOS) approach that resulted in the generation of a set of libraries of compounds presenting novel structural cores. These chemical cores have been employed to design potential antagonists of the antiapoptotic protein Bcl-x(L) through reiterated steps of molecular docking calculations followed by experimental verification of binding. Our data suggest that the DOS approach is suitable to generate novel scaffolds, which can be employed to target protein-protein interactions.

  DOI：

  10.1021/jm9010687
• 作为产物：
  描述：

  (1S,2S,3S,4R)-methyl 3-(N-((R)-1-(benzylcarbamoyl)(phenyl)methyl)-N-benzylamino)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以86%的产率得到(R)-2-(N-benzyl-N-((1R,2S,3R,4S)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl)amino)-N-benzyl-2-phenylacetamide
  参考文献：
  名称：

  Straightforward stereoselective synthesis of polyfunctionalised cyclohexenols using a multicomponent approach

  摘要：

  An intramolecular Ugi 5-centre-4-component reaction (U-5C-4CR) followed by a palladium-catalysed ring-opening has been employed to transform oxabicycloheptene-based beta-amino acids into two families of regioisomeric polyfunctionalised cyclohexenols. The whole process is completely stereoselective and enantiomerically pure products are obtained in high overall yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.097

文献信息

• Identification of Lead Compounds As Antagonists of Protein Bcl-x_L with a Diversity-Oriented Multidisciplinary Approach
  作者：Simone Di Micco、Romina Vitale、Maurizio Pellecchia、Michele F. Rega、Renata Riva、Andrea Basso、Giuseppe Bifulco

  DOI：10.1021/jm9010687

  日期：2009.12.10

  We report on the use of a diversity oriented synthesis (DOS) approach that resulted in the generation of a set of libraries of compounds presenting novel structural cores. These chemical cores have been employed to design potential antagonists of the antiapoptotic protein Bcl-x(L) through reiterated steps of molecular docking calculations followed by experimental verification of binding. Our data suggest that the DOS approach is suitable to generate novel scaffolds, which can be employed to target protein-protein interactions.
• Straightforward stereoselective synthesis of polyfunctionalised cyclohexenols using a multicomponent approach
  作者：Andrea Basso、Luca Banfi、Giuseppe Guanti、Renata Riva

  DOI：10.1016/j.tet.2010.01.097

  日期：2010.3

  An intramolecular Ugi 5-centre-4-component reaction (U-5C-4CR) followed by a palladium-catalysed ring-opening has been employed to transform oxabicycloheptene-based beta-amino acids into two families of regioisomeric polyfunctionalised cyclohexenols. The whole process is completely stereoselective and enantiomerically pure products are obtained in high overall yields. (C) 2010 Elsevier Ltd. All rights reserved.