2-(2-bromophenyl)-N-phenylacetamide | 120230-90-2

• 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-(2-bromophenyl)-N-phenylacetamide
• 英文别名: (2-bromo-phenyl)-acetic acid anilide；(2-Brom-phenyl)-essigsaeure-anilid
• CAS: 120230-90-2
• 化学式: C₁₄H₁₂BrNO
• 分子量: 290.159
• InChiKey: JNGXQZODGCIMEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  470.7±28.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-N-phenylacetamide 在 palladium diacetate caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以82%的产率得到N-苯基吲哚酮
  参考文献：
  名称：

  微波辅助顺序酰胺键形成和分子内酰胺化：快速进入功能化的吲哚。

  摘要：

  已经开发了用于合成N-取代的羟吲哚的通用方法。此两步过程涉及在2-卤代芳酸与各种烷基胺和苯胺之间首先形成微波辅助的酰胺键，然后在水性条件下进行钯催化的分子内酰胺化反应。在烷基胺的情况下，该过程可以一锅法进行，而无需分离中间体酰胺。[结构：见文字]

  DOI：

  10.1021/ol0473804
• 作为产物：
  描述：

  邻溴氰苄 在 氢氧化钾 作用下， 生成 2-(2-bromophenyl)-N-phenylacetamide
  参考文献：
  名称：

  Iodine deficiency in Calabria: Characterization of endemic goiter and analysis of different indicators of iodine status region-wide

  摘要：

  The distribution of goiter prevalence in schoolchildren (no.=13,984, age 6-14 yr), the neonatal TSH results obtained from the congenital hypothyroidism screening program and the urinary iodine excretion values (no.=284) were employed for the assessment of iodine deficiency in Calabria, a Southern Italy region. Data were collected during the years 1990-1996. In the inland territory, goiter prevalence ranged from 19 to 64%. At sea level, there was a great variability of goiter prevalence, with values varying from 5.3 to 25.7%. The analysis of the neonatal hypothyroidism screening program data (no.=21,078) showed a 14.8% frequency of TSH levels >5 muU/ml whole blood in newborns from the inland territory and a 14.1% frequency at sea level. Urinary iodine excretion resulted (mean+/-SD) 53.8+/-43.4 mug/l (range: <20 to 189 mu g/1) in the inland territory and 89.6+/-59.8 mu g/l (range: 26 to 333 mu g/l) at sea level. Median urinary iodine excretion values in 13 villages or small towns of the inland territory ranged from 31 to 57 mu g/l. In 2 major towns located at sea level, the median iodine excretion values were 72 mu g/l in Crotone main city and 94 mu g/l in Reggio Calabria main city. The data indicated that moderate, with pockets of severe iodine deficiency is present in the inland region while iodine supply varies from sufficient to marginally low in the coastal areas. Mild iodine deficiency was found in a major town located at sea level.

  DOI：

  10.1007/bf03343991

文献信息

• Copper-catalyzed transformation of alkyl nitriles to <i>N</i>-arylacetamide using diaryliodonium salts
  作者：Romain Sallio、Pierre-Adrien Payard、Paweł Pakulski、Iryna Diachenko、Indira Fabre、Sabine Berteina-Raboin、Cyril Colas、Ilaria Ciofini、Laurence Grimaud、Isabelle Gillaizeau

  DOI：10.1039/d1ra02305e

  日期：——

  This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.

  这项工作报告了一种简单有效的方法，用于使用环保的二芳基碘鎓盐对烷基腈进行铜催化的氧化还原中性转化并生成N-芳基乙酰胺。该方法效率高、底物范围广、官能团耐受性好。
• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• BF₃·OEt₂-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles
  作者：Chuangchuang Xu、Jiaxi Xu

  DOI：10.1039/c9ob02428j

  日期：——

  Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ

  实现了串联的梅因瓦尔德重排和亲核取代的环氧乙烷腈。在微波辐射下，在三氟化硼的存在下，由3-芳基环氧乙烷-2-甲腈与胺，醇或水容易地合成丙烯酸酯衍生物，设计的合成策略包括将氰基离去基团引入芳基环氧化物中并捕获原位生成的化合物。有毒的氰化物与三氟化硼，使反应高效，安全且对环境无害。该反应通过酸促进的Meinwald重排发生，产生芳基乙酰基氰化物，然后与含氮或氧的亲核胺，醇或水进行加成-消除过程。当前方法为串联Meinwald重排提供了新的应用。
• Copper-catalyzed tandem oxidative cyclization of arylacetamides: efficient access to N-functionalized isatins
  作者：Jie Sun、Bingxin Liu、Bin Xu

  DOI：10.1039/c3ra40657a

  日期：——

  An efficient copper-catalyzed synthesis of N-substituted isatins has been developed in good yields from easily accessible arylacetamides. A wide range of electronically and structurally varied nitrogen fragments could be assembled through this tandem C–O/C–N bond-forming process by tuning the reaction conditions.

  已经开发出一种高效的铜催化合成N-取代异烟酸的反应，能够从易于获得的芳基乙酰胺中以良好的产率合成。通过调整反应条件，可以组装多种电子和结构各异的氮基片段，采用这种串联C–O/C–N键形成的过程。
• 一种α-羟基酰胺类化合物的合成方法
  申请人：安徽师范大学

  公开号：CN103755584B

  公开（公告）日：2016-02-17

  本发明提供了一种α-羟基酰胺类化合物的合成方法,具体包括以下步骤：（1）将酰胺、碱以及二甲基亚砜混合，在空气气氛中密封，反应;（2）反应结束后，冷却到室温，加入饱和食盐水洗涤，用乙酸乙酯萃取3-5次，合并有机层，无水硫酸钠干燥，减压浓缩，得粗产物;（3）粗产物经柱色谱分离提纯，即得所需的α-羟基酰胺类化合物。跟现有技术相比，本发明在氢氧化钾/二甲基亚砜这一简单体系中进行，避免使用复杂或昂贵的催化剂；原料易制备；温度适当，操作易控制；利用空气为绿色氧化剂一步直接得到目标产物；反应高效，产率高达98%，有利工业化生产。