N-(4-acetylphenyl)-2-bromobenzamide | 303122-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-acetylphenyl)-2-bromobenzamide
• CAS: 303122-59-0
• 化学式: C₁₅H₁₂BrNO₂
• mdl: MFCD00432224
• 分子量: 318.17
• InChiKey: MTSLLHXTZOTBBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  381.1±27.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-acetylphenyl)-2-bromobenzamide 在 锂硼氢 、 palladium diacetate 、 sodium hydride 、 caesium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 生成 5-butyl-2-hydroxymethylphenanthridin-6(5H)-one
  参考文献：
  名称：

  Structure–activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand

  摘要：

  Retinoic acid receptor-related orphan receptors (RORs), which belong to the nuclear receptor superfamily, regulate many physiological processes, including hepatic gluconeogenesis, lipid metabolism, immune function and circadian rhythm. Since RORs resemble liver X receptors (LXRs) in the fold structure of their ligand-binding domains, we speculated that ROR-mediated transcription might be modulated by LXR ligands, in line with the multi-template hypothesis. Therefore, we screened our LXR ligand library for compounds with ROR ligand activity and identified a novel ROR ligand with a phenanthridin-6(5H)-one skeleton. Structure-activity relationship studies aimed at separating ROR inverse agonistic activity from LXR-agonistic activity enabled us to develop a series of ROR inverse agonists based on the phenanthridin-6(5H)-one skeleton, including a ROR gamma-selective inverse agonist. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.007
• 作为产物：
  描述：

  4-氨基苯乙酮 、 2-溴苯甲酰氯 在 吡啶 作用下， 生成 N-(4-acetylphenyl)-2-bromobenzamide
  参考文献：
  名称：

  使用 DMSO/HCOONa·2H2O 系统对卤代羧酸衍生物进行还原加氢脱卤

  摘要：

  开发了使用 DMSO/HCOONa·2H 2 O 系统对卤代羧酸衍生物进行实用且操作简单的加氢脱卤。该协议避免了光照射、电化学装置、过渡金属、自由基引发剂、强碱和其他附加添加剂的参与。对照实验表明，HCOONa 可能在通过亲核取代或加成实现加氢脱卤的还原过程中充当氢化物供体。

  DOI：

  10.1021/acs.orglett.3c00782

文献信息

• Structure–activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand
  作者：Yuko Nishiyama、Masahiko Nakamura、Takashi Misawa、Madoka Nakagomi、Makoto Makishima、Minoru Ishikawa、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2014.03.007

  日期：2014.5

  Retinoic acid receptor-related orphan receptors (RORs), which belong to the nuclear receptor superfamily, regulate many physiological processes, including hepatic gluconeogenesis, lipid metabolism, immune function and circadian rhythm. Since RORs resemble liver X receptors (LXRs) in the fold structure of their ligand-binding domains, we speculated that ROR-mediated transcription might be modulated by LXR ligands, in line with the multi-template hypothesis. Therefore, we screened our LXR ligand library for compounds with ROR ligand activity and identified a novel ROR ligand with a phenanthridin-6(5H)-one skeleton. Structure-activity relationship studies aimed at separating ROR inverse agonistic activity from LXR-agonistic activity enabled us to develop a series of ROR inverse agonists based on the phenanthridin-6(5H)-one skeleton, including a ROR gamma-selective inverse agonist. (C) 2014 Elsevier Ltd. All rights reserved.
• Reductive Hydrodehalogenation of Halogenated Carboxylic Acid Derivatives Using a DMSO/HCOONa·2H₂O System
  作者：Guyue Liu、Feiyue Hao、Lingling Liang、Zhengneng Jin、Jiashou Wu

  DOI：10.1021/acs.orglett.3c00782

  日期：2023.4.21

  A practical and operationally simple hydrodehalogenation of halogenated carboxylic acid derivatives using a DMSO/HCOONa·2H2O system is developed. This protocol avoids the involvement of light irradiation, electrochemical apparatus, transition metals, radical initiators, strong bases, and other additional additives. Control experiments suggest that HCOONa might function as a hydride donor in the reduction

  开发了使用 DMSO/HCOONa·2H 2 O 系统对卤代羧酸衍生物进行实用且操作简单的加氢脱卤。该协议避免了光照射、电化学装置、过渡金属、自由基引发剂、强碱和其他附加添加剂的参与。对照实验表明，HCOONa 可能在通过亲核取代或加成实现加氢脱卤的还原过程中充当氢化物供体。