2-(3-methylphenyl)-N-phenylacetamide | 85275-03-2

• 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-(3-methylphenyl)-N-phenylacetamide
• CAS: 85275-03-2
• 化学式: C₁₅H₁₅NO
• mdl: MFCD08071988
• 分子量: 225.29
• InChiKey: TZEIJRBSEOHBMM-UHFFFAOYSA-N

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：
  0.13
• 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-(3-methylphenyl)-N-phenylacetamide 在 [Cu(CH₃CN)₂(PPh₃)₂][ClO₄] 、 五氯化磷 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 1-(4-(phenylamino)cyclopent-2-enyl)-2-m-tolylethanone
  参考文献：
  名称：

  The Diels–Alder Cyclization of Ketenimines

  摘要：

  A Diels-Alder reaction between cyclopentadiene and a variety of ketenimines is reported. A copper(I)-bis(phosphine complex catalyzes the cycloaddition across the C=N bond of the ketenimine in a [4 + 2] reaction to give an enamine intermediate that is hydrolyzed upon purification to generate aminoketones.

  DOI：

  10.1021/ol300742t
• 作为产物：
  描述：

  间甲基苯乙腈 、 苯胺 在 copper doped mesoporous polymelamine-formaldehyde 作用下， 以 水 为溶剂， 反应 14.0h， 以83%的产率得到2-(3-methylphenyl)-N-phenylacetamide
  参考文献：
  名称：

  Nitrogen enriched mesoporous organic polymer anchored copper(ii) material: an efficient and reusable catalyst for the synthesis of esters and amides from aromatic systems

  摘要：

  新的介孔聚合物锚定醋酸铜（Cu-mPMF）已经合成并得到了良好的表征。该复合物的催化性能已经用于酯和酰胺的合成测试。

  DOI：

  10.1039/c4dt03838j

文献信息

• An efficient protocol for the preparation of amides by copper-catalyzed reactions between nitriles and amines in water
  作者：Xiaoya Li、Zhengkai Li、Hang Deng、Xiangge Zhou

  DOI：10.1016/j.tetlet.2013.02.058

  日期：2013.5

  The reactions between nitriles and amines catalyzed by Cu(OAc)2 and 2-piperidinecarboxylic acid were carried out in pure water without any other additives. A variety of substituted amides can be obtained in moderate to good yields up to 90%.

  Cu（OAc）2和2-哌啶羧酸催化的腈和胺之间的反应在纯水中进行，没有任何其他添加剂。可以以中等到良好的产率（高达90％）获得各种取代的酰胺。
• Palladium-catalyzed synthesis of arylacetamides from arylboronic acids
  作者：Ya-Zhen Duan、Min-Zhi Deng

  DOI：10.1016/s0040-4039(03)00586-0

  日期：2003.4

  Aryl amides were synthesized by the palladium catalyzed cross-coupling reaction of alpha-bromoacetamides with arylboronic acids in good yields. Both electron-donating and electron-withdrawing substituents on the aromatic ring are found to be compatible. The addition of Cu2O and PPh3 was found to be essential for good reaction yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs
  作者：Thomas P. Blackburn、Barry Cox、Allen J. Guildford、David J. Le Count、Derek N. Middlemiss、Robert J. Pearce、Craig W. Thornber

  DOI：10.1021/jm00395a013

  日期：1987.12

  A series of 2-[(2-aminoethyl)thio]quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists. The affinity of the compounds for 5-HT1 receptor sites was measured by their ability to displace [3H]-5-HT from rat brain synaptosomes whereas the affinity for 5-HT2 receptor sites was measured by their ability to displace [3H]spiperone from synaptosomes prepared from rat brain cortex. The 5-HT2 antagonist properties of the compounds were measured in vivo by their antagonism of 5-hydroxytryptophan-induced head twitches in the mouse and by their antagonism of hyperthermia induced by fenfluramine (N-ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochloride) in the rat. The structure-activity relationships in this series are discussed and the properties of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline hydrochloride (70) are highlighted.
• Nitrogen enriched mesoporous organic polymer anchored copper(<scp>ii</scp>) material: an efficient and reusable catalyst for the synthesis of esters and amides from aromatic systems
  作者：Rostam Ali Molla、Md. Asif Iqubal、Kajari Ghosh、Kamaluddin Kamaluddin、Sk. Manirul Islam

  DOI：10.1039/c4dt03838j

  日期：——

  New mesoporous polymer anchored copper acetate (Cu-mPMF) has been synthesized and well characterized. The catalytic performance of this complex has been tested for the synthesis of esters and amides.

  新的介孔聚合物锚定醋酸铜（Cu-mPMF）已经合成并得到了良好的表征。该复合物的催化性能已经用于酯和酰胺的合成测试。
• The Diels–Alder Cyclization of Ketenimines
  作者：Jeremy Erb、Jessica Strull、David Miller、Jean He、Thomas Lectka

  DOI：10.1021/ol300742t

  日期：2012.4.20

  A Diels-Alder reaction between cyclopentadiene and a variety of ketenimines is reported. A copper(I)-bis(phosphine complex catalyzes the cycloaddition across the C=N bond of the ketenimine in a [4 + 2] reaction to give an enamine intermediate that is hydrolyzed upon purification to generate aminoketones.