2-Acetamido-5-bromophenyl Acetate | 91715-77-4

• 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-Acetamido-5-bromophenyl Acetate
• 英文别名: 2-acetamido-5-bromophenylacetate；3-Acetoxy-4-acetamino-brombenzol；2-Acetamido-5-bromphenylacetat；(2-acetamido-5-bromophenyl) acetate
• CAS: 91715-77-4
• 化学式: C₁₀H₁₀BrNO₃
• 分子量: 272.098
• InChiKey: KKGGWLPGHXRYOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Acetamido-5-bromophenyl Acetate 在 arsenic oxide 、 硫酸 作用下， 以 甘油 为溶剂， 以33%的产率得到6-溴喹啉-8-醇
  参考文献：
  名称：

  Improved syntheses of some monochloro- and monobromo-8-quinolinols

  摘要：

  Procedures were developed for the preparation of the 2-, 3-, 4-, and 6-monosubstituted chloro and bromo 8-quinolinols which afforded greater yields and/or reduced the number of steps in the preparation. 100 MHz H-1-NMR spectra for the 12 possible monochloro and monobromo analogues are given.

  DOI：

  10.1007/bf00823423
• 作为产物：
  描述：

  N,N,O-三乙酰基-2-氨基苯酚 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-Acetamido-5-bromophenyl Acetate
  参考文献：
  名称：

  Reexamination of the thermolytic rearrangement of 4-halophenyl azides to 2-aminophenols and other products

  摘要：

  The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied. With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken. It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966).

  DOI：

  10.1007/bf00814133

文献信息

• Direct Ortho-Acetoxylation of Anilides via Palladium-Catalyzed sp² C−H Bond Oxidative Activation
  作者：Guan-Wu Wang、Ting-Ting Yuan、Xue-Liang Wu

  DOI：10.1021/jo8003088

  日期：2008.6.1

  Various anilides have been directly ortho-acetoxylated through a Pd(OAc)2-catalyzed C−H bond activation process. The amide group in anilides was found to functionalize as an elegant directing group to convert aromatic sp2 C−H bonds into C−O bonds in high regioselectivity with acetic acid as the acetate source and K2S2O8 as the oxidant.

  通过Pd（OAc）2催化的CH键活化过程，各种苯甲酸酯已直接被邻乙酰氧基化。发现在苯甲酸酯中的酰胺基团作为优雅的引导基团起作用，以乙酸为乙酸盐源和K 2 S 2 O 8为氧化剂以高区域选择性将芳族sp 2 C-H键转变为C-O键。
• Syntheses of heterocyclic compounds. Part XIV. Oxazoles from the pyrolysis of aryl azides in a mixture of a carboxylic and polyphosphoric acid
  作者：R. Garner、E. B. Mullock、H. Suschitzky

  DOI：10.1039/j39660001980

  日期：——

  Aromatic azides with a para-substituent decompose thermally in a mixture of polyphosphoric and a carboxylic acid to give oxazoles, or in some case NO-diacyl o-aminophenols, in good yield. Various aspects of this nitrene mechanism are discussed.

  具有对位取代基的芳族叠氮化物在多磷酸和羧酸的混合物中热分解，从而以良好的收率得到恶唑，或在某些情况下为NO-二酰基邻氨基苯酚。讨论了该氮烯机理的各个方面。
• Smalley,R.K.; Suschitzky,H., Journal of the Chemical Society, 1963, p. 5571 - 5572
  作者：Smalley,R.K.、Suschitzky,H.

  DOI：——

  日期：——
• Reexamination of the thermolytic rearrangement of 4-halophenyl azides to 2-aminophenols and other products
  作者：H. Gershon、D. D. Clarke、M. Gershon

  DOI：10.1007/bf00814133

  日期：1993.4

  The halogenation of derivatives of 2-aminophenol with N-chloro- and N-bromosuccinimides at ambient temperatures in acetic acid was studied. With the necessary compounds available, a reexamination of the thermolytic rearrangement of 2-halophenyl azides to 2-aminophenols and other products was undertaken. It is certain that the rearrangement of 4-halophenyl azides to 2-aminophenols occurs but the products identified in this study differ significantly from those reported previously by Suschitzky et al. (1963, 1966).
• Improved syntheses of some monochloro- and monobromo-8-quinolinols
  作者：Herman Gershon、Donald D. Clarke

  DOI：10.1007/bf00823423

  日期：1991.11

  Procedures were developed for the preparation of the 2-, 3-, 4-, and 6-monosubstituted chloro and bromo 8-quinolinols which afforded greater yields and/or reduced the number of steps in the preparation. 100 MHz H-1-NMR spectra for the 12 possible monochloro and monobromo analogues are given.