ethyl (E)-2-cyano-3-(naphthalen-2-yl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (E)-2-cyano-3-(naphthalen-2-yl)acrylate
• 英文别名: Ethyl 2-cyano-trans-3-(2-naphthyl)acrylate；ethyl (E)-2-cyano-3-naphthalen-2-ylprop-2-enoate
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: OCPOYALXTVXRED-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-cyano-3-(naphthalen-2-yl)acrylate 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以35%的产率得到4,6-bis(4-naphthyl)-3,5-dicyano-5-ethoxycarbonyl-2-piperidinone
  参考文献：
  名称：

  One-Pot Formation of Functionalised 2-Piperidinones from Arylidenecyanoacetates and Methanolic Ammonia via Tandem Reactions

  摘要：

  Aryl aldehydes react with ethyl cyanoacetate in methanolic ammonium acetate to expeditiously furnish, besides high yields of arylidenecyanoacetates, 4,6-diaryt-3,5-dicyano-5-ethoxycarbonyl-2-piperidinones in low yields. But preformed arylidenecyanoacetates react with methanolic ammonia to furnish the same functionalised 2-piperidinones in much better yields. The actual stereostructure of one of the products was determined by single crystal X-ray diffraction analysis, and novel tandem reactions occurring in one pot are proposed for the formation of the products.

  DOI：

  10.3987/com-07-s(u)59
• 作为产物：
  描述：

  2-萘甲醛 、 氰乙酸乙酯 在 xonotlite 、 potassium tert-butylate 作用下， 反应 1.0h， 以89%的产率得到ethyl (E)-2-cyano-3-(naphthalen-2-yl)acrylate
  参考文献：
  名称：

  Knoevenagel缩合反应的催化

  摘要：

  单独的硬硅钙石或通过叔丁醇钾的掺杂使碱性硬硅钙石更为碱性，可催化芳族醛与丙二腈或氰基乙酸烷基酯之间的标题反应。在环境温度下，此程序可特别提供高收率的E烯烃Knoevenagel产品。

  DOI：

  10.1016/s0040-4039(00)88928-5

文献信息

• Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation
  作者：Dennis Kühbeck、G. Saidulu、K. Rajender Reddy、David Díaz Díaz

  DOI：10.1039/c1gc15925a

  日期：——

  The effectiveness of neutral pH chitosan hydrogel beads (CSHB) as a green organocatalyst for a variety of C–C bond forming reactions (i.e. aldol reaction, Knoevenagel condensation, nitroaldol (Henry) reaction, Michael addition) has been comprehensively evaluated. Reaction rates, conversions and selectivities were studied as a function of a series of input variables including size, pH and reactive surface area of the beads, catalyst loading, temperature, molecular weight of the biopolymer, concentration, solvent system and molar ratio of reactants. Moreover, the catalytic biohydrogel beads were characterized by a variety of techniques including, among others, SEM, FT-IR, TGA and DSC.

  中性pH壳聚糖水凝胶珠（CSHB）作为一种绿色有机催化剂，在多种C-C键形成反应（例如醛醇反应、Knoevenagel缩合反应、硝基醛醇（Henry）反应、Michael加成反应）中的有效性已得到全面评估。研究了反应速率、转化率和选择性随一系列输入变量（包括珠子大小、pH值、反应表面面积、催化剂负载量、温度、生物聚合物分子量、浓度、溶剂体系和反应物摩尔比）的变化情况。此外，通过多种技术手段（包括扫描电镜（SEM）、傅里叶变换红外光谱（FT-IR）、热重分析（TGA）和差示扫描量热法（DSC））对催化性生物水凝胶珠进行了表征。
• Development of the First Two-Pore Domain Potassium Channel TWIK-Related K⁺ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity
  作者：Delphine Vivier、Ismail Ben Soussia、Nuno Rodrigues、Stéphane Lolignier、Maïly Devilliers、Franck C. Chatelain、Laetitia Prival、Eric Chapuy、Geoffrey Bourdier、Khalil Bennis、Florian Lesage、Alain Eschalier、Jérôme Busserolles、Sylvie Ducki

  DOI：10.1021/acs.jmedchem.6b01285

  日期：2017.2.9

  development of a novel class of analgesic drugs, suggesting that activation of TREK-1 could result in pain inhibition. Here, we report the synthesis of a series of substituted acrylic acids (1–54) based on our previous work with caffeate esters. The analogues were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid-induced

  TWIK相关的K +通道TREK-1最近已成为开发新型镇痛药的有吸引力的治疗靶标，表明TREK-1的激活可能导致疼痛抑制。在这里，我们报告了一系列取代的丙烯酸（合成1 - 54）基于我们以前的咖啡酸酯酯的工作。通过电生理学评估了类似物调节TREK-1通道的能力以及体内抗伤害感受活性（乙酸诱导的扭体法和热板法），从而鉴定出了一系列能够激活TREK-1的新型分子。并在体内显示出强大的抗伤害感受活性。呋喃基类似物36是该系列中最有前途的。
• A rhodium-catalysed conjugate addition/cyclization cascade for the asymmetric synthesis of 2-amino-4<i>H</i>-chromenes
  作者：Zhiqian Chang、Huilong Zhu、Changhui Wu、Junhao Xing、Xiaowei Dou

  DOI：10.1039/d0ob02404j

  日期：——

  enantioselective synthesis of 2-amino-4H-chromenes via the cascade rhodium-catalysed conjugate addition/hetero Thorpe–Ziegler reaction is reported. Moderate to good yields (up to 98%) and high enantioselectivities (up to 92% ee) were obtained with a chiral diene-coordinated rhodium complex as the catalyst. This protocol remedies the methodological deficiency in the asymmetric synthesis of 4-aryl 2-amino-4H-chromenes

  据报道，通过级联的铑催化的共轭加成反应/杂类索普-齐格勒反应，对氨基选择性合成2-氨基-4 H-色烯。使用手性二烯配位的铑配合物作为催化剂，可获得中等至良好的收率（高达98％）和高的对映选择性（高达92％ee）。该方案弥补了4-芳基2-氨基-4 H-色烯不对称合成中的方法学缺陷。
• Multiple Absolute Stereocontrol in Pd-Catalyzed [3+2] Cycloaddition of Oxazolidinones and Trisubstituted Alkenes Using Chiral Ammonium–Phosphine Hybrid Ligands
  作者：Naomichi Imagawa、Yuya Nagato、Kohsuke Ohmatsu、Takashi Ooi

  DOI：10.1246/bcsj.20160053

  日期：2016.6.15

  The development of a Pd-catalyzed highly enantio- and diastereoselective [3+2] cycloaddition of 5-vinyloxazolidinones and activated trisubstituted alkenes is described in detail. This protocol for ...

  详细描述了 Pd 催化的 5-乙烯基恶唑烷酮和活化的三取代烯烃的高度对映选择性和非对映选择性 [3+2] 环加成的发展。该协议用于...
• Catalyst-Free [3 + 3] Annulation/Oxidation of Cyclic Amidines with Activated Olefins: When the Substrate Olefin Is Also an Oxidant
  作者：Wendan Han、Yuanhang Li、Kaki Raveendra Babu、Jing Li、Yuhai Tang、Yong Wu、Silong Xu

  DOI：10.1021/acs.joc.1c00717

  日期：2021.6.4

  DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants

  在此，我们描述了环脒如 DBU（1,8-二氮杂双环（5.4.0）undec-7-ene）和 DBN（1,5-二氮杂双环（4.3 .0)non-5-ene)与活化的烯烃，即2-亚芳基丙二腈和2-氰基-3-芳基丙烯酸酯，分别提供三环2-吡啶酮和吡啶-2(1 H )-亚胺。该机制是基于 DFT 计算提出的。在反应中，环脒作为环化的C，N-双亲核试剂，而烯烃通过作为反应物和氧化剂发挥双重作用。

表征谱图