摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(E)-N-phenyl-3-(p-tolyl)acrylamide

中文名称
——
中文别名
——
英文名称
(E)-N-phenyl-3-(p-tolyl)acrylamide
英文别名
(E)-3-(p-tolyl)-N-phenylacrylamide;N-Phenyl-4-methylcinnamamide;(E)-3-(4-methylphenyl)-N-phenylprop-2-enamide
(E)-N-phenyl-3-(p-tolyl)acrylamide化学式
CAS
——
化学式
C16H15NO
mdl
——
分子量
237.301
InChiKey
GQTUDGSMSDCDOA-VAWYXSNFSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4
  • 重原子数:
    18
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.06
  • 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:
    (E)-N-phenyl-3-(p-tolyl)acrylamide 在 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 tributylmethylammonium dibutyl phosphate 作用下, 以 1,2-二氯乙烷 为溶剂, 以58%的产率得到7-methyl-1-phenylquinolin-2(1H)-one
    参考文献:
    名称:
    Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C–H Amidation
    摘要:
    A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (E-T) transfer based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.
    DOI:
    10.1021/acs.orglett.7b03600
  • 作为产物:
    描述:
    1-甲基-4-(3-苯基丙-2-炔基)苯甲酸盐酸羟胺2,3-二氯-5,6-二氰基-1,4-苯醌 作用下, 以 乙腈 为溶剂, 反应 12.0h, 以52%的产率得到(E)-N-phenyl-3-(p-tolyl)acrylamide
    参考文献:
    名称:
    通过三步串联反应 将芳基丙炔直接转化为丙烯酰胺†
    摘要:
    使用DDQ作为氧化剂,可以通过sp 3 C–H和C–C键断裂在芳基丙炔和羟胺盐酸盐之间形成一种新颖且无金属的丙烯酰胺。机理研究表明,丙烯酰胺是通过三步串联序列形成的,包括交叉脱氢偶联(CDC)反应,Aza-Meyer-Schuster重排和Beckmann重排。
    DOI:
    10.1039/c3ob42444h
点击查看最新优质反应信息

文献信息

  • DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement
    作者:Jun Qiu、Ronghua Zhang
    DOI:10.1039/c3ob41218k
    日期:——
    An atom-efficient and transition metal-free approach to amides from the corresponding benzyl hydrocarbons through C–H and C–C bond cleavage has been developed. Mechanistic studies have shown that a DDQ-promoted cross-dehydrogenative coupling (CDC) reaction with subsequent oxidation and rearrangement are involved in this transformation.
    开发了一种通过C-H和C-C键断裂,从相应的苄基烃高效、无需过渡金属的原子到酰胺合成的方法。机理研究表明,这种转化涉及DDQ促进的交叉脱氢偶联(CDC)反应、随后氧化和重排。
  • Direct Amidation of Carboxylic Acids with Nitroarenes
    作者:Shao-Peng Wang、Chi Wai Cheung、Jun-An Ma
    DOI:10.1021/acs.joc.9b02068
    日期:2019.11.1
    N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium
    N-芳基酰胺是药物和农业化学中重要的一类化合物。对N-芳基酰胺的快速且低成本的合成仍然有很高的需求。本文中,我们公开了一种操作简单的方法,可直接从容易获得的硝基芳烃和羧酸作为偶联底物直接获得N-芳基酰胺。该方法涉及将羧酸原位活化为酰氧基phosph盐以进行一锅酰胺化,而无需分离相应的合成中间体。此外,制备和后处理的简便性允许快速有效地合成多种N-芳基酰胺,包括几种基于酰胺的类药物和农用化学分子。
  • Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
    作者:Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu
    DOI:10.1002/ejoc.201500010
    日期:2015.4
    synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation
    在2,3-二氯-5存在下,以仲醇、Cu(ClO4)2·6H2O为催化剂,以叠氮化三甲基甲硅烷(TMSN3)为氮源,探索了一种温和、简便的酰胺合成方法。 ,6-二氰基对苯醌 (DDQ) 在环境温度下。该方法已成功地适用于直接从其相应的醇制备叠氮化物,并在 ω-卤代叠氮化物的形成和烯丙醇在苄醇部分存在下的叠氮化中提供出色的化学选择性。此外,该策略为合成可作为 β-氨基酸前体的叠氮化物提供了机会。
  • Manganese(I) Catalyzed α-Alkenylation of Amides Using Alcohols with Liberation of Hydrogen and Water
    作者:Biplab Keshari Pandia、Chidambaram Gunanathan
    DOI:10.1021/acs.joc.1c00685
    日期:2021.8.6
    Herein, unprecedented manganese-catalyzed direct α-alkenylation of amides using alcohols is reported. Aryl amides are reacted with diverse primary alcohols, which provided the α,β-unsaturated amides in moderate to good yields with excellent selectivity. Mechanistic studies indicate that Mn(I) catalyst oxidizes the alcohols to their corresponding aldehydes and also plays an important role in efficient
    在此,报道了使用醇对酰胺进行前所未有的锰催化直接 α-烯基化。芳基酰胺与多种伯醇反应,以中等至良好的收率和优异的选择性提供 α,β-不饱和酰胺。机理研究表明,Mn(I) 催化剂将醇类氧化成相应的醛类,并且在通过羟醛缩合有效形成 C=C 键方面也发挥着重要作用。通过在催化系统中操作的芳构化-脱芳构化过程,金属-配体协同促进了这种选择性烯化。生物可再生醇被用作烯基化试剂,用于酰胺的具有挑战性的 α-烯基化,以高丰度的贱金属锰为催化剂,其结果是水和二氢作为唯一的副产物,
  • Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
    作者:Xiao-Feng Wu、Bo Chen
    DOI:10.1055/s-0037-1610753
    日期:2020.5
    A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
    通过异氰酸酯与链烯基铝试剂的直接偶联,开发了一种用于合成线性 α,β-不饱和酰胺的新方法。在室温下,在没有任何催化剂或添加剂的情况下,所需的 α,β-不饱和酰胺以良好的收率和良好的官能团耐受性分离出来。
查看更多