N-[3-(2-bromoacetyl)-2-fluoro-6-phenylmethoxyphenyl]methanesulfonamide | 948575-89-1

• 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-(2-bromoacetyl)-2-fluoro-6-phenylmethoxyphenyl]methanesulfonamide
• CAS: 948575-89-1
• 化学式: C₁₆H₁₅BrFNO₄S
• 分子量: 416.268
• InChiKey: MUKRNFVIEZNULZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-(2-bromoacetyl)-2-fluoro-6-phenylmethoxyphenyl]methanesulfonamide 在 咪唑 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Arylpropanolamines: Selective β3 agonists arising from strategies to mitigate phase I metabolic transformations

  摘要：

  Utilization of N-substituted-4-hydroxy-3-methylsulfonanilidoethanolamines I as selective beta(3) agonists is complicated by their propensity to undergo metabolic oxidative N-dealkylation, generating 0.01-2% of a very potent alpha(1) adrenergic agonist 2. A summary of the SAR for this hepatic microsomal conversion precedes presentation of strategies to maintain the advantages of chemotype I while mitigating the consequences of N-dealkylation. This effort led to the identification of 4-hydroxy-3-methylsulfonanilidopropanolamines 15 for which the SAR for the unique stereochemical requirements for binding to the P adrenergic receptors culminated in the identification of the potent, selective 03 agonist 15f (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.030
• 作为产物：
  描述：

  1-(2-Fluoro-4-hydroxy-3-nitrophenyl)ethanone 在 吡啶 、 溴 、 sodium hydride 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[3-(2-bromoacetyl)-2-fluoro-6-phenylmethoxyphenyl]methanesulfonamide
  参考文献：
  名称：

  Arylpropanolamines: Selective β3 agonists arising from strategies to mitigate phase I metabolic transformations

  摘要：

  Utilization of N-substituted-4-hydroxy-3-methylsulfonanilidoethanolamines I as selective beta(3) agonists is complicated by their propensity to undergo metabolic oxidative N-dealkylation, generating 0.01-2% of a very potent alpha(1) adrenergic agonist 2. A summary of the SAR for this hepatic microsomal conversion precedes presentation of strategies to maintain the advantages of chemotype I while mitigating the consequences of N-dealkylation. This effort led to the identification of 4-hydroxy-3-methylsulfonanilidopropanolamines 15 for which the SAR for the unique stereochemical requirements for binding to the P adrenergic receptors culminated in the identification of the potent, selective 03 agonist 15f (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.030