N-(1-(4-acetylphenyl)vinyl)acetamide | 823790-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(1-(4-acetylphenyl)vinyl)acetamide
• 英文别名: N-[1-(4-Acetylphenyl)ethenyl]acetamide
• CAS: 823790-71-2
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: ARMMJBKWFPLMGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-(4-acetylphenyl)vinyl)acetamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以57 mg的产率得到1,4-二乙酰苯
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u
• 作为产物：
  描述：

  1-(4-acetylphenyl)ethanol 在 ([2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru(CO)(μ-CO))2 、 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 N-(1-(4-acetylphenyl)vinyl)acetamide
  参考文献：
  名称：

  利用N ？的亲核性。H亚胺：由烷基叠氮化物和酸酐合成酰胺

  摘要：

  在与酸酐的反应中，研究了由烷基叠氮化物通过钌催化反应生成的N-未取代亚胺的亲核性。最初的产物是N-酰亚胺，其异构化为相应的酰胺。加热或三乙胺促进了在室温下稳定的N-酰亚胺的异构化。在温和条件下成功合成了各种含各种官能团的无环和环状酰胺。除乙酸酐外，还可使用各种酸酐。从与环状酸酐的反应中，获得含有羧酸基的酰胺。

  DOI：

  10.1002/adsc.201400584

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed olefinic C–H alkynylation of enamides at room temperature
  作者：Chao Feng、Daming Feng、Teck-Peng Loh

  DOI：10.1039/c4cc04072d

  日期：——

  Rh(iii)-catalyzed C–H olefinic alkynylation of enamides for the stereospecific construction of synthetically useful Z-type enynamides is reported. This protocol displays good functionality tolerance and operational simplicity thus providing an alternative synthetic opportunity for the ease of access to specific 1,3-enyne derivatives.

  报告了Rh（III）催化的烯酰胺的C-H烯烃炔基化反应，用于立体特异性构建具有合成用途的Z型烯炔酰胺。该方案显示出良好的官能团容忍性和操作简便性，从而为轻松获取特定的1,3-炔烯衍生物提供了另一种合成机会。
• METHOD FOR PREPARING ENAMIDE COMPOUND AND RUTHENIUM COMPLEX CATALYST USED THEREIN
  申请人：POSTECH ACADEMY-INDUSTRY FOUNDATION

  公开号：US20170291885A1

  公开（公告）日：2017-10-12

  Provided is a method for preparing an enamide compound, which includes reacting an organic azide compound having α-hydrogen and an anhydride by addition of a ruthenium complex catalyst in the presence of an ionic liquid, and a ruthenium complex catalyst used herein.

  提供了一种制备烯酰胺化合物的方法，包括在存在离子液体的情况下，通过向具有α-氢的有机叠氮化合物和酸酐添加钌配合物催化剂来反应，并且这里使用的是一种钌配合物催化剂。
• Synthesis of Enamides by Ruthenium-Catalyzed Reaction of Alkyl Azides with Acid Anhydrides in Ionic Liquid
  作者：Han Kyu Pak、Junghoon Han、Mina Jeon、Yongjin Kim、Yearang Kwon、Jin Yong Park、Young Ho Rhee、Jaiwook Park

  DOI：10.1002/cctc.201500935

  日期：2015.12

  Enamides were synthesized by a ruthenium‐catalyzed one‐pot, one‐step procedure from alkyl azides and acid anhydrides. The substrate scope includes not only secondary azides, but also primary aliphatic ones to give a wide range of enamides containing various functional groups. This one‐step procedure was based on the newly discovered activity of Severin's diruthenium complex ([Cp^RuCl2]2: Cp^=η5‐1‐methoxy‐2

  通过钌催化的一步法，一步法由烷基叠氮化物和酸酐合成酰胺。底物的范围不仅包括仲叠氮化物，而且还包括伯脂族伯酸，以得到各种包含各种官能团的酰胺。这种一步程序是基于塞韦林的二钌复合物（混合[Cp ^的RuCl的新发现的活性2 ] 2：的Cp ^ =η 5 -1-甲氧基-2,4-二-叔-丁基-3-新戊基环戊二烯基），用于将烷基叠氮化物转化为离子液体中相应的NH亚胺中间体。在Severin配合物与叠氮化物的化学计量反应中观察到钌四烯配合物的形成，烷基化叠氮化物充当了NH亚胺中间体的形成催化剂。
• 유기 아자이드 및 아실 주개로부터 엔아마이드를 제조하는 방법
  申请人：POSTECH Research and Business Development Foundation 포항공과대학교 산학협력단(220040433361) BRN ▼506-82-07303

  公开号：KR20160059189A

  公开（公告）日：2016-05-26

  본 발명은 유기 아자이드 화합물로부터 질소에 치환기가 없는 이민을 발생시키고, 그와 아실 주개와의 반응을 통해 엔아마이드 화합물을 합성하는 방법에 관한 것이다. 본 발명의 제조 방법을 이용하면, 적절한 촉매를 사용하여 알파 수소를 가진 유기 아자이드로부터 연속한 질소 제거 및 1,2-수소 옮김 반응을 통해 질소에 치환기가 없는 이민을 생성하고, 이 이민과 아실 주개를 반응시켜 엔아마이드 화합물을 합성할 수 있다.

  本发明涉及一种从有机酰胺化合物中引发无氮取代基的迁移，并通过其与酰基试剂的反应合成恩酰胺化合物的方法。利用本发明的制备方法，可以使用适当的催化剂，通过连续氮脱除和1,2-氢迁移反应从具有α-氢的有机酰胺生成无氮取代基的迁移，然后将该迁移与酰基试剂反应来合成恩酰胺化合物。
• A general method for regioselective Heck arylation of electron-rich N-acyl-N-vinylamine with aryl halides
  作者：Zhihua Liu、Dan Xu、Weijun Tang、Lijin Xu、Jun Mo、Jianliang Xiao

  DOI：10.1016/j.tetlet.2008.02.144

  日期：2008.4

  A highly efficient protocol for the Pd-catalyzed regioselective Heck arylation of the electron-rich olefin N-acyl-N-vinylamine with aryl halides has been developed. In the presence of hydrogen-bond donor [H2NiPr2][BF4] as an additive, this proceeds smoothly in isopropanol to afford exclusively the branched products in high yields.

  已经开发出用于富电子的烯烃N-酰基-N-乙烯基胺与芳基卤化物的Pd催化区域选择性Heck芳基化的高效方案。在存在氢键供体[H 2 N i Pr 2 ] [BF 4 ]作为添加剂的情况下，该过程在异丙醇中顺利进行，从而以高收率独家提供支链产物。