N-(3-苯基苯基)乙酰胺 | 2113-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-苯基苯基)乙酰胺
• 英文名称: N-(biphenyl-3-yl)acetamide
• 英文别名: N-([1,1'-biphenyl]-3-yl)acetamide；3-phenylacetanilide；N-acetyl-3-phenylaniline；N-biphenyl-3-yl-acetamide；N-Biphenyl-3-yl-acetamid；3-Acetamino-diphenyl；3-Acetamidobiphenyl；N-(3-phenylphenyl)acetamide
• CAS: 2113-54-4
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: IRMSAKOLFSBQJH-UHFFFAOYSA-N

物化性质

• 熔点：
  148°C
• 沸点：
  350.95°C (rough estimate)
• 密度：
  1.0694 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 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

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(3-苯基苯基)乙酰胺 在 溴 作用下， 生成 N-(6-bromo-biphenyl-3-yl)-acetamide
  参考文献：
  名称：

  Tandem optimization of target activity and elimination of mutagenic potential in a potent series of N-aryl bicyclic hydantoin-based selective androgen receptor modulators

  摘要：

  Pharmacokinctic studies in cynomolgus monkeys with a novel prototype selective androgen receptor modulator revealed trace amounts of an aniline fragment released through hydrolytic metabolism. This aniline fragment was determined to be mutagenic in an Ames assay. subsequent concurrent optimization for target activity and avoidance of mutagenicity led to the identification of a pharmacologically superior clinical candidate without mutagenic potential. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.076
• 作为产物：
  描述：

  5,6-二氢-[1,1’-联苯]-3(4H)-酮 在 4-二甲氨基吡啶 、 盐酸羟胺 、 sodium acetate 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三环戊基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 N-(3-苯基苯基)乙酰胺
  参考文献：
  名称：

  Pd-Catalyzed Semmler–Wolff Reactions for the Conversion of Substituted Cyclohexenone Oximes to Primary Anilines

  摘要：

  Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd-0(PCy3)(2), and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.

  DOI：

  10.1021/ja4073172

文献信息

• Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionali­zation
  作者：Bernd Schmidt、Nelli Elizarov、Nastja Riemer、Frank Hölter

  DOI：10.1002/ejoc.201500795

  日期：2015.9

  Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.

  与它们的邻位对应物不同，间和对乙酰氨基苯胺可以转化为相应的乙酰氨基芳烃重氮盐。这些为多种 Pd 催化的芳烃官能化反应提供了各种机会，例如 Matsuda-Heck-、Suzuki-Miyaura- 或 Fujiwara-Moritani 偶联。
• Direct <i>para</i>-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
  作者：Yujie Chen、Zhibin Huang、Yaqiqi Jiang、Sai Shu、Shan Yang、Da-Qing Shi、Yingsheng Zhao

  DOI：10.1021/acs.joc.1c00681

  日期：2021.6.18

  Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most

  已实现碘(III)介导的碘苯合成4-碘-N-苯基苯胺，反应条件温和。各种官能团具有良好的耐受性，以中等至良好的产率提供相应的产品。剩余的碘基团为将产品转化为几种有价值的不对称二苯胺提供了一个有效的平台。最重要的是，该反应可以轻松放大到 10 克规模，突出了其合成效用。机理研究表明，原位生成的芳基高价碘中间体是实现这种对位选择性 C-H 胺化反应的关键因素。
• (NHC)Palladium Complexes from Hydroxy-Functionalized Imidazolium Salts as Catalyst for the Microwave-Accelerated Fluorine-Free Hiyama Reaction
  作者：Itziar Peñafiel、Isidro M. Pastor、Miguel Yus、Miguel A. Esteruelas、Montserrat Oliván、Enrique Oñate

  DOI：10.1002/ejoc.201101110

  日期：2011.12

  Financial support from the Ministerio de Ciencia e Innovacion (MICINN) of Spain (Project Nos. CTQ2007-65218, CTQ2008- 00810, Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (PROMETEO/2009/0349 and FEDER), the Diputacion General de Aragon (E35), and the European Social Fund is acknowledged.

  来自西班牙创新科技部长 (MICINN)（项目编号 CTQ2007-65218、CTQ2008-00810、Consolider Ingenio 2010 CSD2007-00006）、Generalitat Valenciana (PROMETEO/2007-00009) 和 Generalitat de Aragon (E35) 和欧洲社会基金。
• Nickel-catalyzed hydrogenolysis of unactivated carbon–cyano bonds
  作者：Tuhin Patra、Soumitra Agasti、Atanu Modak、Debabrata Maiti

  DOI：10.1039/c3cc44562c

  日期：——

  Selective hydrogenolysis of C-CN bonds can allow chemists to take advantage of ortho-directing ability, alpha-C-H acidity and electron withdrawing ability of the cyano group for synthetic manipulations. We have discovered hydrogenolysis of aryl and aliphatic cyanides under just 1 bar of hydrogen by using a nickel catalyst. This protocol was applied in the aryl cyanide directed functionalization reaction

  C-CN键的选择性氢解可让化学家利用氰基的邻位导向能力，α-CH酸度和吸电子能力进行合成操作。我们已经发现，通过使用镍催化剂，仅在1 bar的氢气下就可以芳基和脂肪族氰化物进行氢解。该方案适用于芳基氰化物指导的官能化反应和苄基氰化物的α-取代。
• Nickel-Catalyzed Suzuki–Miyaura Coupling of Heteroaryl Ethers with Arylboronic Acids
  作者：Xiao-Jian Li、Jin-Ling Zhang、Yu Geng、Zhong Jin

  DOI：10.1021/jo4005537

  日期：2013.5.17

  Nickel-catalyzed Suzuki–Miyaura coupling of heteroaryl ethers with arylboronic acids was described. Selective activation of the phenol C–O bonds was achieved by converting them into the corresponding aryl 2,4-dimethoxy-1,3,5-triazine-6-yl ethers, in which aryl C–O bond could be selectively cleaved with inexpensive, air-stable NiCl2(dppf) as a catalyst. Coupling of these readily accessible heteroaryl

  镍催化杂芳基醚与芳基硼酸的铃木-宫浦偶合。苯酚C-O键的选择性活化是通过将其转化为相应的芳基2,4-二甲氧基-1,3,5-三嗪-6-基醚来实现的，其中芳基C-O键可以用廉价的方法选择性裂解。 ，空气稳定的NiCl 2（dppf）作为催化剂。这些易于获得的杂芳基醚的偶联被证明对广泛的官能团具有耐受性。