6,7-dibromo-2H-pyrrolo[1,2-a]pyrazin-1-one | 290353-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 6,7-dibromo-2H-pyrrolo[1,2-a]pyrazin-1-one
• 英文别名: 6,7-dibromo-1H,2H-pyrrolo[1,2-a]pyrazin-1-one
• CAS: 290353-35-4
• 化学式: C₇H₄Br₂N₂O
• mdl: MFCD21608508
• 分子量: 291.93
• InChiKey: DVJXLGFDWSCHKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,7-dibromo-2H-pyrrolo[1,2-a]pyrazin-1-one 在 sodium hydride 、 calcium oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 CCDC-614039
  参考文献：
  名称：

  通过三组分咪唑烷酮二元醇盐合成全细胞生长的海洋天然产物Dibromophakellstatin。

  摘要：

  来自海洋海绵Phakellia mauritiana的四环吡咯-咪唑生物碱二溴环已抑菌素已从吡咯经七个步骤合成，总收率为18％。关键步骤是三环烯酰胺，腈和氨基甲酰基结构单元的三组分组装，一步即可得到二溴环己汀的咪唑烷酮环。值得注意的是，可以将具有双重功能的试剂EtO 2 CNHOTs用作亲电子腈和偶极氨基甲酰基组分的来源。使用脱溴的前体双吡咯并吡嗪酮可以提高高得率，并允许我们开发第二代合成方法。确认了二溴泛函他汀的细胞抑制活性。

  DOI：

  10.1021/jo061813u
• 作为产物：
  描述：

  2,2,2-三氯-1-(4,5-二溴-1H-吡咯-2-基)-1-乙酮 在 甲烷磺酸 、 对甲苯磺酸 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 132.0h， 生成 6,7-dibromo-2H-pyrrolo[1,2-a]pyrazin-1-one
  参考文献：
  名称：

  Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of β-amido aldehydes and revised structure of synthetic homolongamide

  摘要：

  DOI：

  10.1016/s0040-4039(00)00630-4

文献信息

• Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of β-amido aldehydes and revised structure of synthetic homolongamide
  作者：Ana Carolina Barrios Sosa、Kenichi Yakushijin、David A Horne

  DOI：10.1016/s0040-4039(00)00630-4

  日期：2000.6
• ——
  作者：Thomas Lindel、Holger Hoffmann、Matthias Hochgürtel、Joseph R. Pawlik

  DOI：10.1023/a:1005591826613

  日期：——

  We investigated the relationship between the structures of pyrrole-containing alkaloids from marine sponges of the genus Agelas and their capacity to deter feeding by the omnivorous Caribbean reef fish, Thalassoma bifasciatum. Seven natural products were assayed at volumetric concentrations of 1, 5, and 10 mg/ml: dispacamide A, keramadine, oroidin, midpacamide, 4,5-dibromopyrrole-2-carboxylic acid, 4,5-dibromopyrrole-2-carboxamide, and racemic longamide A. We also assayed 14 structural analogs obtained mostly by chemical synthesis. Of the seven natural products, only rac-longamide A was not significantly deterrent at any of the assay concentrations. The pyrrole moiety was required for feeding inhibition activity, while the addition of the imidazole group enhanced this activity. Variously functionalized imidazoles lacking the pyrrole moiety were not deterrent. Combinations of the natural products appeared to have an additive effect on feeding inhibition; there was no evidence of synergy. Given their high concentrations in sponge tissue, dispacamide A and oroidin most probably serve as the primary chemical defenses of many Agelas sp., while minor compounds such as keramadine are not present in high enough concentrations to contribute much to chemical defense.
• Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation
  作者：Michael Zöllinger、Peter Mayer、Thomas Lindel

  DOI：10.1021/jo061813u

  日期：2006.12.1

  The tetracyclic pyrrole−imidazole alkaloid dibromophakellstatin from the marine sponge Phakellia mauritiana has been synthesized within seven steps from pyrrole in an 18% overall yield. The key step is a three-component assembly of a tricyclic enamide, a nitrene, and a carbamoyl building block, affording the imidazolidinone ring of dibromophakellstatin in one step. Notably, it is possible to employ

  来自海洋海绵Phakellia mauritiana的四环吡咯-咪唑生物碱二溴环已抑菌素已从吡咯经七个步骤合成，总收率为18％。关键步骤是三环烯酰胺，腈和氨基甲酰基结构单元的三组分组装，一步即可得到二溴环己汀的咪唑烷酮环。值得注意的是，可以将具有双重功能的试剂EtO 2 CNHOTs用作亲电子腈和偶极氨基甲酰基组分的来源。使用脱溴的前体双吡咯并吡嗪酮可以提高高得率，并允许我们开发第二代合成方法。确认了二溴泛函他汀的细胞抑制活性。