1-(5-溴戊-4-炔基)哌啶-2,6-二酮 | 143261-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(5-溴戊-4-炔基)哌啶-2,6-二酮
• 英文名称: N-(5-bromopent-4-ynyl) glutarimide
• 英文别名: 2,6-Piperidinedione, 1-(5-bromo-4-pentynyl)-；1-(5-bromopent-4-ynyl)piperidine-2,6-dione
• CAS: 143261-18-1
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: OHOYXBKOLZPLEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-溴戊-4-炔基)哌啶-2,6-二酮 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 9-(dibromomethylidene)octahydro-4H-quinolizin-4-one
  参考文献：
  名称：

  Cousson, Alain; Gazeau, Catherine; Gesson, Jean-Pierre, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 1, p. 95 - 104

  摘要：

  DOI：
• 作为产物：
  描述：

  1-pent-4-ynyl-1-piperidine-2,6-dione 在 silver nitrate N-溴代丁二酰亚胺(NBS) 作用下， 以 丙酮 为溶剂， 以91%的产率得到1-(5-溴戊-4-炔基)哌啶-2,6-二酮
  参考文献：
  名称：

  1-Bromalkynes as π-nucleophiles in acyliminium ion cyclilizations. a formal synthesis of lupinine and epilupinine.

  摘要：

  The use of a 1-bromoalkyne as pi-nucleophile in the alpha-N-acyliminium ion cyclization of a glutarimide derivative results in the formation of a single bromoenol triflate 11 in triflic acid-trifluoroacetic and of a mixture (E/Z: 4/1) of bromofluoro derivatives 12a,b in HF, 11 is quantitatively converted to esters 9a,b which are also obtained after trifluoroscetic acid treatment and methanolysis. 9a,b are known precursors of lupinine and epilupinine.

  DOI：

  10.1016/s0040-4039(00)92521-8

文献信息

• Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and <i>Z</i>-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides
  作者：Xuejun Zhang、Yanshi Zhang、Jian Huang、Richard P. Hsung、Kimberly C. M. Kurtz、Jossian Oppenheimer、Matthew E. Petersen、Irina K. Sagamanova、Lichun Shen、Michael R. Tracey

  DOI：10.1021/jo060230h

  日期：2006.5.1

  method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry

  在此描述了用于将各种酰胺与炔基溴化物偶联的通用且有效的方法。这种新颖的酰胺化反应涉及使用五水合硫酸铜（II）和1,10-菲咯啉来指导sp-C-N键形成的催化方案，从而通过分子内酰胺化形成结构上多样的酰胺，包括大环酰胺。鉴于对酰胺化学的浓厚兴趣，这种原子经济的酰胺合成方法应引起有机合成界的进一步关注。
• 1-Bromalkynes as π-nucleophiles in acyliminium ion cyclilizations. a formal synthesis of lupinine and epilupinine.
  作者：J.P. Gesson、J.C. Jacquesy、D. Rambaud

  DOI：10.1016/s0040-4039(00)92521-8

  日期：1992.6

  The use of a 1-bromoalkyne as pi-nucleophile in the alpha-N-acyliminium ion cyclization of a glutarimide derivative results in the formation of a single bromoenol triflate 11 in triflic acid-trifluoroacetic and of a mixture (E/Z: 4/1) of bromofluoro derivatives 12a,b in HF, 11 is quantitatively converted to esters 9a,b which are also obtained after trifluoroscetic acid treatment and methanolysis. 9a,b are known precursors of lupinine and epilupinine.
• Cousson, Alain; Gazeau, Catherine; Gesson, Jean-Pierre, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 1, p. 95 - 104
  作者：Cousson, Alain、Gazeau, Catherine、Gesson, Jean-Pierre、Jacquesy, Jean-Claude、Rambaud, Didier、Renoux, Brigitte

  DOI：——

  日期：——