(E)-2-(5-bromo-4-oxopent-2-en-1-yl)isoindoline-1,3-dione | 160072-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-2-(5-bromo-4-oxopent-2-en-1-yl)isoindoline-1,3-dione
• 英文别名: 2-(5-Bromo-4-oxopent-2-enyl)isoindole-1,3-dione；2-[(E)-5-bromo-4-oxopent-2-enyl]isoindole-1,3-dione
• CAS: 160072-68-4
• 化学式: C₁₃H₁₀BrNO₃
• 分子量: 308.131
• InChiKey: HAADRIFTETVULV-ONEGZZNKSA-N

物化性质

• 沸点：
  431.8±40.0 °C(Predicted)
• 密度：
  1.591±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-bromo-4-oxopent-2-en-1-yl)isoindoline-1,3-dione 在 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 100.0h， 生成 N-[5-((E)-3-Amino-propenyl)-1H-imidazol-2-yl]-acetamide
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021
• 作为产物：
  描述：

  苯二甲酰亚氨基乙醛 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 21.0h， 生成 (E)-2-(5-bromo-4-oxopent-2-en-1-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021

文献信息

• Synthesis of Branched Triubiquitin Active-Site Directed Probes
  作者：Jiaan Liu、Yanfeng Li、Kirandeep K. Deol、Eric R. Strieter

  DOI：10.1021/acs.orglett.9b02406

  日期：2019.9.6

  proteasome-targeting signals for aggregation-prone proteins and cell cycle regulators. By implementing a new synthetic strategy for the electrophilic warhead, we herein report on the generation and reactivity of a series of branched triubiquitin active-site directed probes. These new tools can be used to dissect the molecular basis of branched chain assembly and disassembly.

  活性位点定向探针是研究泛素结合和解结合机制的强大工具。支链泛素链已成为易于聚集的蛋白质和细胞周期调节剂的重要蛋白酶体靶向信号。通过实施亲电子弹头的新合成策略，我们在此报告了一系列分支三泛素活性位点定向探针的生成和反应性。这些新工具可用于剖析支链组装和拆卸的分子基础。
• METHOD OF GENERATING LINKAGE-SPECIFIC DI-AND POLYPROTEIN PROBES
  申请人：ZHUANG Zhihao

  公开号：US20160237471A1

  公开（公告）日：2016-08-18

  Deubiquitinating enzyme (DUB) probes are provided that resemble native diubiquitin (diUB) with a similar linkage size and that may contain a Michael acceptor for trapping the DUB active-site cysteine. For example, both K63- and K48-linked diubiquitin probes are generated using a facile chemical ligation method, utilizing the linker compound 3-(2-(bromomethyl)-1,3-dioxolan-2-yl)prop-2-en-1-amine. The diUb probes are capable of labelling DUBs from different families and may be employed to reveal intrinsic linkage specificities of DUBs.
• US9605297B2
  申请人：——

  公开号：US9605297B2

  公开（公告）日：2017-03-28
• [EN] METHOD OF GENERATING LINKAGE-SPECIFIC DI-AND POLYPROTEIN PROBES<br/>[FR] PROCÉDÉ DE GÉNÉRATION DE SONDES DE DIPROTÉINE ET POLYPROTÉINE SPÉCIFIQUES D'UNE LIAISON
  申请人：ZHUANG ZHIHAO

  公开号：WO2015057803A1

  公开（公告）日：2015-04-23

  Deubiquitinating enzyme (DUB) probes are provided that resemble native diubiquitin (diUB) with a similar linkage size and that may contain a Michael acceptor for trapping the DUB active-site cysteine. For example, both K63- and K48-linked diubiquitin probes are generated using a facile chemical ligation method, utilizing the linker compound 3-(2- (bromomethyl)-1,3-dioxolan-2-yl)prop-2-en-1 -amine. The diUb probes are capable of labelling DUBs from different families and may be employed to reveal intrinsic linkage specificities of DUBs.