N-[3-[(1R)-2-bromo-1-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]benzenesulfonamide | 848072-78-6

• 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: N-[3-[(1R)-2-bromo-1-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]benzenesulfonamide
• CAS: 848072-78-6
• 化学式: C₂₀H₂₈BrNO₃SSi
• 分子量: 470.503
• InChiKey: PDBMRNSDJNEWEZ-IBGZPJMESA-N

物化性质

• 沸点：
  496.2±55.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[3-[(1R)-2-bromo-1-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]benzenesulfonamide 在 盐酸 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 、 乙腈 为溶剂， 生成 [3-[(2R)-2-[[(2R)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]-1H-indol-7-yl] methanesulfonate
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

  摘要：

  The continued SAR investigation of tryptamine-based human beta(3)-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent beta(3)-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for beta(3)-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.033
• 作为产物：
  描述：

  (R)-2-bromo-1-(tert-butyldimethylsilyloxy)-1-(3-nitrophenyl)ethane 在 吡啶 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-[3-[(1R)-2-bromo-1-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]benzenesulfonamide
  参考文献：
  名称：

  Tryptamine-based human β3-adrenergic receptor agonists. Part 3: Improved oral bioavailability via modification of the sulfonamide moiety

  摘要：

  The continued SAR investigation of tryptamine-based human beta(3)-adrenergic receptor (AR) agonists is reported. Prior efforts resulted in the identification of 2 as a potent beta(3)-AR agonist. Further modification of the left side arylsulfonamide portion in 2 provided compounds with good cell permeability, which have potent agonistic activity for beta(3)-AR. Cinnamylamine analog 16i exhibited an excellent agonistic profile in vitro and good oral bioavailability in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.033