(2S,3¹R,7aS,10R,10aS)-methyl 8-oxo-10-(phenylthio)dodecahydroazepino[3,2,1-hi]indole-2-carboxylate | 1422688-56-9

• 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: (2S,3¹R,7aS,10R,10aS)-methyl 8-oxo-10-(phenylthio)dodecahydroazepino[3,2,1-hi]indole-2-carboxylate
• 英文别名: methyl (2S,4S,5R,8S,13R)-7-oxo-5-phenylsulfanyl-1-azatricyclo[6.4.1.04,13]tridecane-2-carboxylate
• CAS: 1422688-56-9
• 化学式: C₂₀H₂₅NO₃S
• 分子量: 359.489
• InChiKey: ZDJLYLZJIKADCR-WCWVYFQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3¹R,7aS,10R,10aS)-methyl 8-oxo-10-(phenylthio)dodecahydroazepino[3,2,1-hi]indole-2-carboxylate 在 三乙胺 作用下， 以 二氯甲烷-D2 为溶剂， 生成 8-oxo-(1,2S,4,7,7aS,8,10aR,10bS)-decahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Influence of Base and Structure in the Reversible Covalent Conjugate Addition of Thiol to Polycyclic Enone Scaffolds

  摘要：

  The energetics of thiol addition and elimination reactions to bicyclic enones derived from an indole core structure were explored using H-1 NMR and density functional theory (DFT) calculations. The agreement between experiment and theory is excellent, and the combined results reveal that even minor changes in the conformation of the enone, substituents on the scaffold, and the use of different bases have a signficant influence on product distribution. A potential application of these principles is in the rational design of new reversible covalent enzyme inhibitors.

  DOI：

  10.1021/ol400094k
• 作为产物：
  描述：

  (2S,3¹R,7aS,10R,10aS)-methyl 8-oxo-10-(phenylthio)-1,2,3¹,4,7,7a,8,9,10,10adecahydroazepino[3,2,1-hi]indole-2-carboxylate 在 Wilkinson's catalyst 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 以62%的产率得到(2S,3¹R,7aS,10R,10aS)-methyl 8-oxo-10-(phenylthio)dodecahydroazepino[3,2,1-hi]indole-2-carboxylate
  参考文献：
  名称：

  Influence of Base and Structure in the Reversible Covalent Conjugate Addition of Thiol to Polycyclic Enone Scaffolds

  摘要：

  The energetics of thiol addition and elimination reactions to bicyclic enones derived from an indole core structure were explored using H-1 NMR and density functional theory (DFT) calculations. The agreement between experiment and theory is excellent, and the combined results reveal that even minor changes in the conformation of the enone, substituents on the scaffold, and the use of different bases have a signficant influence on product distribution. A potential application of these principles is in the rational design of new reversible covalent enzyme inhibitors.

  DOI：

  10.1021/ol400094k

文献信息

• Influence of Base and Structure in the Reversible Covalent Conjugate Addition of Thiol to Polycyclic Enone Scaffolds
  作者：Christopher J. Rosenker、Elizabeth H. Krenske、K. N. Houk、Peter Wipf

  DOI：10.1021/ol400094k

  日期：2013.3.1

  The energetics of thiol addition and elimination reactions to bicyclic enones derived from an indole core structure were explored using H-1 NMR and density functional theory (DFT) calculations. The agreement between experiment and theory is excellent, and the combined results reveal that even minor changes in the conformation of the enone, substituents on the scaffold, and the use of different bases have a signficant influence on product distribution. A potential application of these principles is in the rational design of new reversible covalent enzyme inhibitors.