(Z)-N-(1-phenylprop-1-en-2-yl)acetamide

• 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: (Z)-N-(1-phenylprop-1-en-2-yl)acetamide
• 英文别名: N-[(Z)-1-phenylprop-1-en-2-yl]acetamide
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: PSKGJWYQBIGNFH-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (Z)-N-(1-phenylprop-1-en-2-yl)acetamide 在 碘苯二乙酸 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以50%的产率得到2,4-dimethyl-5-phenyloxazole
  参考文献：
  名称：

  Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization

  摘要：

  A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.

  DOI：

  10.1021/jo302073e
• 作为产物：
  描述：

  2-methyl-1-phenyl-1-buten-3-one oxime 在 五氯化磷 作用下， 以 1,4-二氧六环 为溶剂， 生成 (Z)-N-(1-phenylprop-1-en-2-yl)acetamide
  参考文献：
  名称：

  Zielinski,W., Polish Journal of Chemistry, 1978, vol. 52, p. 2233 - 2241

  摘要：

  DOI：

文献信息

• Direct Titanium-Mediated Conversion of Ketones into Enamides with Ammonia and Acetic Anhydride
  作者：Jonathan T. Reeves、Zhulin Tan、Zhengxu S. Han、Guisheng Li、Yongda Zhang、Yibo Xu、Diana C. Reeves、Nina C. Gonnella、Shengli Ma、Heewon Lee、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1002/anie.201107601

  日期：2012.2.6

  A one‐step conversion of ketones into N‐acetyl enamides was developed. The process employs safe and inexpensive reagents, proceeds under mild conditions, and tolerates diverse functional groups. The addition of edte (N,N,N′,N′‐tetrakis(2‐hydroxyethyl)ethylenediamine) prior to workup enables water solubilization of Ti alkoxides and allows a simple extractive workup.

  开发了将酮一步转化为N-乙酰基酰胺的方法。该方法使用安全且廉价的试剂，可在温和条件下进行，并能耐受各种官能团。在后处理前添加edte（N，N，N '，N'-四（2-羟乙基）乙二胺）可使Ti醇盐水溶性化并进行简单的萃取后处理。
• NEW ORTHO-FUNCTIONALIZED P-CHIRAL ARYLPHOSPHINES AND DERIVATIVES: THEIR PREPARATION AND USE IN ASYMMETRIC CATALYSIS
  申请人：Stephan Michel

  公开号：US20100099875A1

  公开（公告）日：2010-04-22

  The invention relates to novel organo phosphorus P-chiral optically active compounds of formula (I) having a hydroxyl, mercapto, amino, carboxyl, sulfonyl group on aryl near a phosphorus atom, to the preparation and the use thereof in then asymmetrical catalysis of unsaturated compounds. Novel acylphosphine optically pure ligands embodied in the form of transition metal complexes exhibit an increased activity and enantloselectivity, in particular in asymmetrical hydrogenation, in comparison with the same type Uganda such as DiPAMP.

  该发明涉及具有化学式（I）的新型有机磷P-手性光学活性化合物，其在含磷原子附近的芳基上具有羟基、巯基、氨基、羧基、磺酰基基团，以及其在不对称催化不饱和化合物中的制备和使用。新型酰基膦光学纯配体以过渡金属配合物的形式体现，与同类型的乌干达化合物（如DiPAMP）相比，在不对称氢化等反应中表现出增强的活性和对映选择性。
• 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。
• Exploiting the Nucleophilicity of NH Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides
  作者：Junghoon Han、Mina Jeon、Han Kyu Pak、Young Ho Rhee、Jaiwook Park

  DOI：10.1002/adsc.201400584

  日期：2014.9.15

  The nucleophilicity of N‐unsubstituted imines, which were generated from alkyl azides by a ruthenium‐catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N‐acylimines, which isomerized to the corresponding enamides. Heating or triethylamine facilitated the isomerization of N‐acylimines that are stable at room temperature. A wide range of acyclic and cyclic

  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。