2-Bromo-3-methoxyacetanilide | 150637-99-3

• 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: 2-Bromo-3-methoxyacetanilide
• 英文别名: 2-bromo-3-methoxy-N-acetylaniline；N-(2-bromo-3-methoxyphenyl)acetamide
• CAS: 150637-99-3
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: BFMOVYIWTNZABD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-3-methoxyacetanilide 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-bromo-3-methoxyphenylamine hydrochloride
  参考文献：
  名称：

  WO2007/53755

  摘要：

  公开号：
• 作为产物：
  描述：

  2,4,6-三溴-3-甲氧基苯胺 在 palladium on activated charcoal sodium hydroxide 、 甲烷磺酸 、 甲酸:三乙胺 1:1 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 2-Bromo-3-methoxyacetanilide
  参考文献：
  名称：

  Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines

  摘要：

  A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.

  DOI：

  10.1016/s0040-4020(01)80400-2

文献信息

• Process for Preparing Substituted Anisidines
  申请人：Gallou Fabrice

  公开号：US20080293972A1

  公开（公告）日：2008-11-27

  Disclosed is a process for preparing substituted anisidines of formula I starting from substituted cyclic hydroxy-ketones II via aromatization through a substituted oxime intermediate IV in which R is C 1 -C 6 alkyl or halogen, and Alk is C 1 -C 6 alkyl. The substituted anisidines of formula I have been found to be useful as intermediates in the preparation of agents for the treatment of hepatitis C viral (HCV) infections.

  本发明揭示了一种制备代替苯胺的方法，该方法从代替的环烷羟基酮II开始，通过取代的肟中间体IV进行芳香化反应，其中R是C1-C6烷基或卤素，Alk是C1-C6烷基。发现式I的代替苯胺在制备治疗丙型肝炎病毒（HCV）感染的药物的中间体方面是有用的。
• Asymmetric Hydrogenation of Phenanthridines with Chiral Boranes
  作者：Guangyu Cui、Xiangqing Feng、Haifeng Du

  DOI：10.1002/cjoc.202300588

  日期：2024.3.15

  The asymmetric hydrogenation of N-heteroarenes provides an efficient method for the synthesis of optically active cyclic secondary amines. In this paper, we described an asymmetric hydrogenation of phenanthridines using a chiral mono-alkene-derived borane. A variety of dihydrophenanthridines were furnished in high yields with up to 93% ee. The current catalytic system was very sensitive for the steric

  N-杂芳烃的不对称氢化为合成光学活性环状仲胺提供了一种有效的方法。在本文中，我们描述了使用手性单烯烃衍生的硼烷对菲啶进行不对称氢化。多种二氢菲啶的产率高达 93% ee。目前的催化系统对菲啶的空间位阻非常敏感。为了获得高对映选择性，菲啶的一个苯基上需要有大的取代基。但C=N键碳上的大量取代基会急剧降低反应活性。
• Optimization of Potent Inhibitors of <i>P. falciparum</i> Dihydroorotate Dehydrogenase for the Treatment of Malaria
  作者：Renato T. Skerlj、Cecilia M. Bastos、Michael L. Booker、Martin L. Kramer、Robert H. Barker、Cassandra A. Celatka、Thomas J. O’Shea、Benito Munoz、Amar Bir Sidhu、Joseph F. Cortese、Sergio Wittlin、Petros Papastogiannidis、Inigo Angulo-Barturen、Maria Belen Jimenez-Diaz、Edmund Sybertz

  DOI：10.1021/ml200143c

  日期：2011.9.8

  Inhibition of dihydroorotate dehydrogenase (DHODH) for P. falciparum potentially represents a new treatment option for malaria, since DHODH catalyzes the rate-limiting step in the pyrimidine biosynthetic pathway and P. falciparum is unable to salvage pyrimidines and must rely on de novo biosynthesis for survival. We report herein the synthesis and structure-activity relationship of a series of 5-(2-methylbenzimidazol-1-yl)-N-alkylthiophene-2-carboxamides that are potent inhibitors against PfDHODH but do not inhibit the human enzyme. On the basis of efficacy observed in three mouse models of malaria, acceptable safety pharmacology risk assessment and safety toxicology profile in rodents, lack of potential drug-drug interactions, acceptable ADME/pharmacokinetic profile, and projected human dose, 5-(4-cyano-2-methyl-1H-benzo[d]imidazol-1-yl)-N-cyclopropylthiophene-2-carboxamide 2q was identified as a potential drug development candidate.
• US7884246B2
  申请人：——

  公开号：US7884246B2

  公开（公告）日：2011-02-08
• Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines
  作者：R.Garth Pews、James E. Hunter、Richard M. Wehmeyer

  DOI：10.1016/s0040-4020(01)80400-2

  日期：1993.5

  A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.