4-bromopyrrole-2-N-methylcarboxamide | 132911-43-4

• 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-bromopyrrole-2-N-methylcarboxamide
• 英文别名: 5MQE；4-bromo-1H-pyrrole-2-carboxylic acid methylamide；4-bromo-N-methyl-1H-pyrrole-2-carboxamide
• CAS: 132911-43-4
• 化学式: C₆H₇BrN₂O
• mdl: MFCD07021324
• 分子量: 203.038
• InChiKey: HQGRBJIXXLIGLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromopyrrole-2-N-methylcarboxamide 在 四磷十氧化物 作用下， 反应 1.0h， 生成 N-甲基-1H-吡咯-2-羧酰胺 、 5-bromo-N-methyl-1H-pyrrole-2-carboxamide 、 4,5-dibromopyrrole-2-N-methylcarboxamide
  参考文献：
  名称：

  钝化吡咯上的酸催化卤素舞

  摘要：

  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。

  DOI：

  10.1002/jhet.276
• 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-bromopyrrole-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

• Substrate Controlled Regioselective Bromination of Acylated Pyrroles Using Tetrabutylammonium Tribromide (TBABr₃)
  作者：Shuang Gao、Travis K. Bethel、Tayeb Kakeshpour、Grace E. Hubbell、James E. Jackson、Jetze J. Tepe

  DOI：10.1021/acs.joc.8b01251

  日期：2018.8.17

  Electrophilic bromination of pyrroles bearing carbonyl substituents at C-2 typically results in a mixture of the 4- and 5-brominated species, generally favoring the 4-position. Herein, we describe a substrate-controlled regioselective bromination in which tetra-butyl ammonium tribromide (TBABr3) reacts with pyrrole-2-carboxamide substrates to yield the 5-brominated species as the predominant (up to

  在C-2处带有羰基取代基的吡咯的亲电溴化反应通常会产生4-溴和5-溴化物质的混合物，通常有利于4-位。在本文中，我们描述了受底物控制的区域选择性溴化反应，其中四丁基三溴化铵（TBABr 3）与吡咯-2-羧酰胺底物反应，生成以5溴化物为主的（高达> 10：1）产物。
• METHODS AND COMPOUNDS FOR THE TREATMENT OF GENETIC DISEASE
  申请人：Design Therapeutics, Inc.

  公开号：US20210238226A1

  公开（公告）日：2021-08-05

  The present disclosure relates to compounds and methods for modulating the expression of dmpk, atxn1, atxn2, atxn3, cacna1a, atxn7, ppp2r2br tbp, htt, jph3r ar, or atn1 and treating diseases and conditions in which dmpk, atxn1, atxn2, atxn3, cacna1a, atxn1, ppp2r2b, tbp, htt, jph3, ar, or atn1 plays an active role. The compound can be a transcription modulator molecule having a first terminus, a second terminus, and oligomeric backbone, wherein: a) the first terminus comprises a DNA-binding moiety capable of noncovalently binding to a nucleotide repeat sequence CAG or CTG; b) the second terminus comprises a protein-binding moiety binding to a regulatory molecule that modulates an expression of a gene comprising the nucleotide repeat sequence CAG or CTG; and c) the oligomeric backbone comprising a linker between the first terminus and the second terminus.
• 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.