1-(4-Bromo-phenyl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester | 846049-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(4-Bromo-phenyl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-(4-bromophenyl)-2-[5-fluoro-6-(trifluoromethyl)-1H-benzimidazol-2-yl]-6-azaspiro[2.5]octane-6-carboxylate
• CAS: 846049-70-5
• 化学式: C₂₆H₂₆BrF₄N₃O₂
• 分子量: 568.409
• InChiKey: FVRQUHPPUBMUKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4-Bromo-phenyl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 0.3h， 生成 4'-[1-(5-flouro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]oct-1-yl]-biphenyl-3-carbonitrile
  参考文献：
  名称：

  Design and synthesis of orally efficacious benzimidazoles as melanin-concentrating hormone receptor 1 antagonists

  摘要：

  Biaryl urea lead compound 1 was discovered earlier in our MCH antagonist program. Novel benzimidazole analogues with increased chemical stability, devoid of the potential carcinogenic liability associated with a biarylamine moiety, were synthesized and evaluated to be potent MCH R1 antagonists. Two compounds in this series have demonstrated in vivo efficacy in a rodent obesity model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.062
• 作为产物：
  描述：

  1-(4-Bromo-phenyl)-1-cyano-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester 在 二异丁基氢化铝 、 sodium hydrogensulfite 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-(4-Bromo-phenyl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design and synthesis of orally efficacious benzimidazoles as melanin-concentrating hormone receptor 1 antagonists

  摘要：

  Biaryl urea lead compound 1 was discovered earlier in our MCH antagonist program. Novel benzimidazole analogues with increased chemical stability, devoid of the potential carcinogenic liability associated with a biarylamine moiety, were synthesized and evaluated to be potent MCH R1 antagonists. Two compounds in this series have demonstrated in vivo efficacy in a rodent obesity model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.062

文献信息

• US7214691B2
  申请人：——

  公开号：US7214691B2

  公开（公告）日：2007-05-08
• Design and synthesis of orally efficacious benzimidazoles as melanin-concentrating hormone receptor 1 antagonists
  作者：Wen-Lian Wu、Duane A. Burnett、Mary Ann Caplen、Martin S. Domalski、Chad Bennett、William J. Greenlee、Brian E. Hawes、Kim O’Neill、Blair Weig、Daniel Weston、Brian Spar、Timothy Kowalski

  DOI：10.1016/j.bmcl.2006.04.062

  日期：2006.7

  Biaryl urea lead compound 1 was discovered earlier in our MCH antagonist program. Novel benzimidazole analogues with increased chemical stability, devoid of the potential carcinogenic liability associated with a biarylamine moiety, were synthesized and evaluated to be potent MCH R1 antagonists. Two compounds in this series have demonstrated in vivo efficacy in a rodent obesity model. (c) 2006 Elsevier Ltd. All rights reserved.