4-[1-(4-Bromo-phenyl)-2-oxo-ethylidene]-piperidine-1-carboxylic acid tert-butyl ester | 846049-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[1-(4-Bromo-phenyl)-2-oxo-ethylidene]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[1-(4-bromophenyl)-2-oxoethylidene]piperidine-1-carboxylate
• CAS: 846049-52-3
• 化学式: C₁₈H₂₂BrNO₃
• 分子量: 380.282
• InChiKey: PUAJIINLKZWOQI-UHFFFAOYSA-N

物化性质

• 沸点：
  503.5±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[1-(4-Bromo-phenyl)-2-oxo-ethylidene]-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 、 sodium hydrogensulfite 、 三氟乙酸 作用下， 以 乙醇 、 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
• 作为产物：
  描述：

  对溴苯乙腈 在 sodium ethanolate 、 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-[1-(4-Bromo-phenyl)-2-oxo-ethylidene]-piperidine-1-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.