(R)-N-allyl-N-(1-(3,5-difluorophenyl)ethyl)-1-(trifluoromethyl)cyclopropane-1-carboxamide | 1338778-00-9

• 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: (R)-N-allyl-N-(1-(3,5-difluorophenyl)ethyl)-1-(trifluoromethyl)cyclopropane-1-carboxamide
• CAS: 1338778-00-9
• 化学式: C₁₆H₁₆F₅NO
• 分子量: 333.301
• InChiKey: MBCLZPUAZGOTEZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-3-bromo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 、 (R)-N-allyl-N-(1-(3,5-difluorophenyl)ethyl)-1-(trifluoromethyl)cyclopropane-1-carboxamide 在 N-甲基二环己基胺 、 bis(tributylphosphine)palladium 0 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1R)-1-(3,5-difluorophenyl)ethyl]-N-[(E)-3-[(3S)-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-yl]prop-2-enyl]-1-(trifluoromethyl)cyclopropane-1-carboxamide
  参考文献：
  名称：

  (E)-Alkenes as replacements of amide bonds: Development of novel and potent acyclic CGRP receptor antagonists

  摘要：

  A new class of CGRP receptor antagonists was identified by replacing the central amide of a previously identified anilide lead structure with ethylene, ethane, or ethyne linkers. (E)-Alkenes as well as alkynes were found to preserve the proper bioactive conformation of the amides, necessary for efficient receptor binding. Further exploration resulted in several potent compounds against CGRP-R with low susceptibility to P-gp mediated efflux. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.027
• 作为产物：
  描述：

  (R)-1-(3,5-二氟苯基)乙胺盐酸盐 、 1-(trifluoromethyl)cyclopropanecarbonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-N-allyl-N-(1-(3,5-difluorophenyl)ethyl)-1-(trifluoromethyl)cyclopropane-1-carboxamide
  参考文献：
  名称：

  (E)-Alkenes as replacements of amide bonds: Development of novel and potent acyclic CGRP receptor antagonists

  摘要：

  A new class of CGRP receptor antagonists was identified by replacing the central amide of a previously identified anilide lead structure with ethylene, ethane, or ethyne linkers. (E)-Alkenes as well as alkynes were found to preserve the proper bioactive conformation of the amides, necessary for efficient receptor binding. Further exploration resulted in several potent compounds against CGRP-R with low susceptibility to P-gp mediated efflux. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.027