benzyl {1-[{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)methyl]prop-2-en-1-yl}carbamate | 1190391-52-6

• 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: benzyl {1-[{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)methyl]prop-2-en-1-yl}carbamate
• 英文别名: benzyl N-[(1R,2S)-1-[tert-butyl(dimethyl)silyl]oxy-1-(3-chlorophenyl)but-3-en-2-yl]carbamate
• CAS: 1190391-52-6
• 化学式: C₂₄H₃₂ClNO₃Si
• 分子量: 446.061
• InChiKey: DSKWGHFWNWHAAU-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[4-(2-oxobut-3-enyl)phenyl]carbamate 、 benzyl {1-[{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)methyl]prop-2-en-1-yl}carbamate 在 Zhan I catalyst 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Design of a novel pyrrolidine scaffold utilized in the discovery of potent and selective human β3 adrenergic receptor agonists

  摘要：

  A novel class of human beta(3)-adrenergic receptor agonists was designed in effort to improve selectivity and metabolic stability versus previous disclosed beta(3)-AR agonists. As observed, many of the beta(3)-AR agonists seem to need the acyclic ethanolamine core for agonist activity. We have synthesized derivatives that constrained this moiety by introduction of a pyrrolidine. This unique modification maintains human beta(3) functional potency with improved selectivity versus ancillary targets and also eliminates the possibility of the same oxidative metabolites formed from cleavage of the N-C bond of the ethanolamine. Compound 39 exhibited excellent functional beta(3) agonist potency across species with good pharmacokinetic properties in rat, dog, and rhesus monkeys. Early de-risking of this novel pyrrolidine core (44) via full AMES study supports further research into various new beta(3)-AR agonists containing the pyrrolidine moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.087
• 作为产物：
  描述：

  1-(3-chlorophenyl)prop-2-en-1-ol 在 咪唑 、 盐酸 、 臭氧 、 copper(II) sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 benzyl {1-[{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)methyl]prop-2-en-1-yl}carbamate
  参考文献：
  名称：

  Design of a novel pyrrolidine scaffold utilized in the discovery of potent and selective human β3 adrenergic receptor agonists

  摘要：

  A novel class of human beta(3)-adrenergic receptor agonists was designed in effort to improve selectivity and metabolic stability versus previous disclosed beta(3)-AR agonists. As observed, many of the beta(3)-AR agonists seem to need the acyclic ethanolamine core for agonist activity. We have synthesized derivatives that constrained this moiety by introduction of a pyrrolidine. This unique modification maintains human beta(3) functional potency with improved selectivity versus ancillary targets and also eliminates the possibility of the same oxidative metabolites formed from cleavage of the N-C bond of the ethanolamine. Compound 39 exhibited excellent functional beta(3) agonist potency across species with good pharmacokinetic properties in rat, dog, and rhesus monkeys. Early de-risking of this novel pyrrolidine core (44) via full AMES study supports further research into various new beta(3)-AR agonists containing the pyrrolidine moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.087