1-溴哌啶-2,6-二酮 | 3699-18-1

• 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-溴哌啶-2,6-二酮
• 英文名称: N-bromoglutarimide
• 英文别名: N-Brom-glutarimid；2,6-Piperidinedione, 1-bromo-；1-bromopiperidine-2,6-dione
• CAS: 3699-18-1
• 化学式: C₅H₆BrNO₂
• 分子量: 192.012
• InChiKey: ZJEQUGWMBSKCCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 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

安全信息

• 海关编码：
  2925190090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  戊二酰亚胺	piperidine-2,6-dione	1121-89-7	C5H7NO2	113.116

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  戊二酰亚胺	piperidine-2,6-dione	1121-89-7	C5H7NO2	113.116

反应信息

• 作为反应物：
  描述：

  1-溴哌啶-2,6-二酮 在 水 作用下， 生成 戊二酰亚胺
  参考文献：
  名称：

  The Return of the Succinimidyl Radical.

  摘要：

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..

  DOI：

  10.3891/acta.chem.scand.52-0062
• 作为产物：
  描述：

  戊二酰亚胺 在 次溴酸 作用下， 生成 1-溴哌啶-2,6-二酮
  参考文献：
  名称：

  的单电子还原ñ -Chlorinated和ñ溴代种自由基源和溴原子形成

  摘要：

  次氯酸（HOCl）和次溴酸（HOBr）是人类的免疫系统产生的强杀菌氧化剂，但与许多人类炎症性疾病（如动脉粥样硬化，哮喘）的发生有关。这些氧化剂容易与含硫和氮的亲核试剂反应，后者会生成N卤代物质（例如，氯胺/溴胺（RR'NX； X = Cl，Br））作为初始产物。氧化还原活性金属离子和超氧自由基（O 2 •−）可以将N卤代物种还原为以氮和碳为中心的自由基。N-卤代物种和O 2 •-它们在炎症部位同时产生，但它们相互作用的重要性仍不清楚。在本研究中，已确定了还原N卤代胺，酰胺和酰亚胺以模拟潜在生物底物的速率常数。水合电子以k 2 > 10 9 M -1 s -1还原这些物质，而O 2 •仅还原具有复杂动力学的N-卤代酰亚胺，这些动力学指示链反应。对于N-溴酰亚胺，N-Br键的异质裂解产生溴原子（Br •），而对于其他底物，N-centered自由基和Cl - /溴-被生产。已使用高级量子化学程

  DOI：

  10.1021/tx100325z

文献信息

• A Practical Synthesis of<i>N</i>-Bromo Imides by Use of Sodium Bromite
  作者：Shoji Kajigaeshi、Takashi Nakagawa、Shizuo Fujisaki、Akiko Nishida

  DOI：10.1246/bcsj.58.769

  日期：1985.2

  N-Bromo imides can be readily prepared under mild conditions by a reaction of imides with sodium bromite in the presence of hydrobromic acid in fairly good yields. The scope and limitation are also presented.

  在温和的条件下，通过亚胺与亚溴酸钠在氢溴酸存在下的反应，可以很容易地制备出 N-溴亚胺，而且产率相当高。本文还介绍了该方法的应用范围和局限性。
• NOUVELLES SYNTHÈSES DE L'ACIDE GLUTARIQUE, DE LA GLUTARIMIDE ET DE L'ACIDE GLUTAMIQUE: PRÉPARATION DE LA N-BROMOGLUTARIMIDE
  作者：Gérard Paris、Roger Gaudry、Louis Berlinguet

  DOI：10.1139/v55-212

  日期：1955.11.1

  not available

  不可用
• Glutarimidyl chemistry: substitution reactions. Mechanism of Ziegler brominations
  作者：U. Luning、S. Seshadri、P. S. Skell

  DOI：10.1021/jo00361a026

  日期：1986.5
• Notes - Reactions of N-Bromoamides and N-Bromoimides with Styrene
  作者：Robert Buckles、William Probst

  DOI：10.1021/jo01363a632

  日期：1957.12.1
• The Return of the Succinimidyl Radical.
  作者：Gábor Merényi、Johan Lind、Lennart Eberson、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0062

  日期：——

  The aqueous kinetics of the succinimidyl radical. S-. has been re-examined in the presence of oxidizable substrates and oxygen. The results indicate a rapid equilibrium between S-. and its ring-opened analogue, the beta B-(isocyanatocarbonyl)ethyl radical, PI.. The equilibrium constant K-1, is ca, 10, with k(1) approximate to 10(7) s(-1) and k(-1) approximate to 10(6) s(-1). The glutarimidyl radical, G(.), was produced by one-electron reduction of N-chloroglutarimide, GCI. The rate constants of several oxidation and hydrogen abstraction reactions with S-. and G(.) have been determined. Furthermore. halogen abstraction reactions from haloimides by some selected alkyl radicals were also scrutinised. Most striking is the finding that the 2-cyanoethyl radical abstracts Br from SBr ca. 25 times slower than does the ethyl radical. This demonstrates a strong beta-effect and rationalises a relatively slow Br abstraction rate by PI. from SBr. While the closure rate of the PI. radical appears to be solvent-insensitive, the ring opening rate of S-., k(1), is estimated to be ca. 100 times faster in, e.g., CH2Cl2, than in water. This suggests hydrogen-bonded stabilisation of S-..