1-methyl-3,3-dibromo-2-piperidone | 49785-78-6

• 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: 1-methyl-3,3-dibromo-2-piperidone
• 英文别名: 3,3-Dibrom-1-methyl-2-piperidon；3,3-dibromo-1-methyl-piperidin-2-one；3,3-Dibromo-1-methylpiperidin-2-one
• CAS: 49785-78-6
• 化学式: C₆H₉Br₂NO
• 分子量: 270.952
• InChiKey: MOLAHZNARGUYSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-3,3-dibromo-2-piperidone 在 盐酸 、 aluminum oxide 、 N-氯代丁二酰亚胺 、 水 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(5-chloro-2,4-dihydroxyphenyl)-5,6-dihydro-6-methylisoxazolo[5,4-c]pyridin-7(4H)-one (9a)
  参考文献：
  名称：

  Synthesis of 5,6-dihydro-4H -benzo[d ]isoxazol-7-one and 5,6-dihydro-4H -isoxazolo[5,4-c ]pyridin-7-one Derivatives as Potential Hsp90 Inhibitors

  摘要：

  A novel class of 5,6‐dihydro‐4H‐benzo[d]isoxazol‐7‐ones and 5,6‐dihydro‐4H‐isoxazolo[5,4‐c]pyridin‐7‐ones was designed, synthesized, and assayed to investigate the affinity toward Hsp90 protein. The synthetic route was based on a 1,3‐dipolar cycloaddition of nitriloxides, generated in situ from suitable benzaldoximes, with 2‐bromocyclohex‐2‐enones or 3‐bromo‐5,6‐dihydro‐1H‐pyridin‐2‐ones. Whereas all the compounds bearing a benzamide group on the bicyclic scaffold were devoid of activity, the derivatives carrying a resorcinol‐like fragment showed a remarkable inhibitory effect on Hsp90. Docking calculations were performed to investigate the orientation of the new compounds within the binding site of the enzyme.

  DOI：

  10.1111/cbdd.12570
• 作为产物：
  描述：

  1-甲基-2-哌啶酮 在 五氯化磷 、 溴 、 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 以54%的产率得到1-methyl-3,3-dibromo-2-piperidone
  参考文献：
  名称：

  Synthesis of 5,6-dihydro-4H -benzo[d ]isoxazol-7-one and 5,6-dihydro-4H -isoxazolo[5,4-c ]pyridin-7-one Derivatives as Potential Hsp90 Inhibitors

  摘要：

  A novel class of 5,6‐dihydro‐4H‐benzo[d]isoxazol‐7‐ones and 5,6‐dihydro‐4H‐isoxazolo[5,4‐c]pyridin‐7‐ones was designed, synthesized, and assayed to investigate the affinity toward Hsp90 protein. The synthetic route was based on a 1,3‐dipolar cycloaddition of nitriloxides, generated in situ from suitable benzaldoximes, with 2‐bromocyclohex‐2‐enones or 3‐bromo‐5,6‐dihydro‐1H‐pyridin‐2‐ones. Whereas all the compounds bearing a benzamide group on the bicyclic scaffold were devoid of activity, the derivatives carrying a resorcinol‐like fragment showed a remarkable inhibitory effect on Hsp90. Docking calculations were performed to investigate the orientation of the new compounds within the binding site of the enzyme.

  DOI：

  10.1111/cbdd.12570

文献信息

• Nilsson, Ingemar; Isaksson, Roland, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 7, p. 531 - 548
  作者：Nilsson, Ingemar、Isaksson, Roland

  DOI：——

  日期：——
• US3951985A
  申请人：——

  公开号：US3951985A

  公开（公告）日：1976-04-20
• US4067985A
  申请人：——

  公开号：US4067985A

  公开（公告）日：1978-01-10