1-(3'-Cyano-biphenyl-4-yl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester | 846049-12-5

• 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: 1-(3'-Cyano-biphenyl-4-yl)-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-(3-cyanophenyl)phenyl]-2-[5-fluoro-6-(trifluoromethyl)-1H-benzimidazol-2-yl]-6-azaspiro[2.5]octane-6-carboxylate
• CAS: 846049-12-5
• 化学式: C₃₃H₃₀F₄N₄O₂
• 分子量: 590.62
• InChiKey: YWBVJXWRBLXMQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3'-Cyano-biphenyl-4-yl)-1-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 以87%的产率得到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-formyl-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester 在 四(三苯基膦)钯 、 sodium carbonate 、 sodium hydrogensulfite 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 0.3h， 生成 1-(3'-Cyano-biphenyl-4-yl)-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