2-{(1-Cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole | 911469-22-2

• 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: 2-{(1-Cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole
• CAS: 911469-22-2
• 化学式: C₃₀H₃₄BF₄N₃O₂
• 分子量: 555.423
• InChiKey: JAMAHECYYQVPHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.38
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-{(1-Cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole 、 5-溴烟腈 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.17h， 生成 5-{4-[(1-cyclopropylmethyl-piperidin-4-ylidene)-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-methyl]-phenyl}-nicotinonitrile
  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：

  4-[(4-Bromo-phenyl)-(5-fluoro-6-trifluoromethyl-1H-benzoimidazol-2-yl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 2-{(1-Cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole
  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