4,5-dibromopyrrole-2-N-methylcarboxamide | 132911-44-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5-dibromopyrrole-2-N-methylcarboxamide
• 英文别名: 4,5-Dibromo-N-methyl-1H-pyrrole-2-carboxamide
• CAS: 132911-44-5
• 化学式: C₆H₆Br₂N₂O
• 分子量: 281.934
• InChiKey: AYBCFAOTERWENJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 溴 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 4,5-dibromopyrrole-2-N-methylcarboxamide
  参考文献：
  名称：

  Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera

  摘要：

  Biologically active extracts of the Caribbean sponge Agelas conifera have yielded, in exhaustive studies, the diacetate salts of seven new bromopyrroles (1, 3-8), as well as that of the known debromooroidin dimer sceptrin (2). These compounds were found to be antiviral and antibacterial and were active in barnacle settlement and biochemical prophage induction assays. The structures assigned were based on spectroscopic comparisons to sceptrin and two-dimensional NMR data. Synthetic bromopyrroles were used to verify bromine substitution patterns. The oxysceptrins (4, 5) are characterized by their aminoimidazolinone group, the ageliferins (6-8) by a unique cyclohexene-based skeleton.

  DOI：

  10.1021/jo00009a008

文献信息

• Acid catalyzed halogen dance on deactivated pyrroles
  作者：Federico Tutino、Gianluca Papeo、Francesca Quartieri

  DOI：10.1002/jhet.276

  日期：——

  A study on the acid catalyzed halogen dance (ACHD) on deactivated bromopyrroles is reported. A different behavior is observed when considering singly deactivated pyrrole alkylcarboxamides, or doubly deactivated pyrroleketo-lactams (aldisines). Although less electron deficient pyrrole alkylcarboxamides suffer from ACHD, the double deactivation on keto-lactams disfavors pyrrole ring protonation thus

  报道了对失活的溴吡咯的酸催化卤素舞（ACHD）的研究。当考虑单独失活的吡咯烷基羧酰胺或双重失活的吡咯酮-内酰胺（醛二胺）时，观察到不同的行为。尽管较少电子缺陷的吡咯烷基羧酰胺遭受ACHD，但酮-内酰胺的双重失活不利于吡咯环的质子化，因此可防止卤素加扰。推测了重排涉及的机制。J.杂环化​​学.2010。
• Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera
  作者：Paul A. Keifer、Robert E. Schwartz、Moustapha E. S. Koker、Robert G. Hughes、Dan Rittschof、Kenneth L. Rinehart

  DOI：10.1021/jo00009a008

  日期：1991.4

  Biologically active extracts of the Caribbean sponge Agelas conifera have yielded, in exhaustive studies, the diacetate salts of seven new bromopyrroles (1, 3-8), as well as that of the known debromooroidin dimer sceptrin (2). These compounds were found to be antiviral and antibacterial and were active in barnacle settlement and biochemical prophage induction assays. The structures assigned were based on spectroscopic comparisons to sceptrin and two-dimensional NMR data. Synthetic bromopyrroles were used to verify bromine substitution patterns. The oxysceptrins (4, 5) are characterized by their aminoimidazolinone group, the ageliferins (6-8) by a unique cyclohexene-based skeleton.