乙基(2E)-2-氰基-3-(4-甲基苯基)丙烯酸酯 | 2017-88-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 乙基(2E)-2-氰基-3-(4-甲基苯基)丙烯酸酯
• 英文名称: ethyl (E)-2-cyano-3-p-tolylacrylate
• 英文别名: ethyl (E)-2-cyano-3-(4-methylphenyl)-2-propenoate；(E)-ethyl 2-cyano-3-p-tolylacrylate；2-Ethoxycarbonyl-3-(4-methylphenyl)-2-propenonitrile；Ethyl 2-cyano-3-(4-methylphenyl)acrylate；ethyl (E)-2-cyano-3-(4-methylphenyl)prop-2-enoate
• CAS: 2017-88-1
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: KKIZDEFOEGGSKX-XYOKQWHBSA-N

物化性质

• 熔点：
  86-89°C
• 沸点：
  160-162 °C(Press: 4 Torr)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  乙基(2E)-2-氰基-3-(4-甲基苯基)丙烯酸酯 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 74.08h， 生成 3-(p-tolyl)pentanedioic acid
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044
• 作为产物：
  描述：

  2-(4-甲基苯基)-1,3-二氧戊环 在 四氢吡咯 、 盐酸 、 溶剂黄146 、 丙酮 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 乙基(2E)-2-氰基-3-(4-甲基苯基)丙烯酸酯
  参考文献：
  名称：

  Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor

  摘要：

  We synthesized methylvesamicol analogs 13-16 and investigated the binding characteristics of 2-[4-phenylpiperidino]cyclohexanol (vesamicol) and methylvesamicol analogs 13-16, with a methyl group introduced into the 4-phenylpiperidine moiety, to sigma receptors (sigma-1, sigma-2) and to vesicular acetylcholine transporters (VAChT) in membranes of the rat brain and liver. In competitive inhibition studies, (-)-o-methylvesamicol [(-)-OMV] (13) (K-i = 6.7 nM), as well as (-)-vesamicol (K-i = 4.4 nM), had a high affinity for VAChT. (+)-p-Methylvesamicol [(+)-PMV] (16) (K-i = 3.0 nM), as well as SA4503 (K-i = 4.4 nM), reported as a sigma-1 mapping agent for positron emission tomography (PET), had a high affinity for the sigma-1 receptor. The binding affinity of (+)-PMV (1-16) for the sigma-1 receptor (K-i = 3.0 nM) was about 13 times higher than that for the sigma-2 (sigma-2) receptor (K-i = 40.7 nM). (+)-PMV (16) (K-i = 199 nM) had a much lower affinity for VAChT than SA4503 (K-i = 50.2 nM) and haloperidol (K-i = 41.4 nM). These results showed that the binding characteristics of (-)-OMV (13) to VAChT were similar to those of (-)-vesamicol and that (+)-PMV (16) bound to the sigma-1 receptor with high affinity. In conclusion, (-)-OMV (13) and (+)-PMV (16). which had a Suitable structure, with a methyl group for labeling with C-11, may become not only a new VAChT ligand and a new type of sigma receptor ligand, respectively, but may also become a new target compound of VAChT and the sigma-1 receptor radioligand for PET, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.044

文献信息

• Phosphane-Catalyzed Knoevenagel Condensation: A Facile Synthesis ofα-Cyanoacrylates andα-Cyanoacrylonitriles
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Ashok K. Basak、Boddapati Visali、Akkirala Venkat Narsaiah、Kommu Nagaiah

  DOI：10.1002/ejoc.200300513

  日期：2004.2

  Triphenylphosphane (TPP) has been utilized as a novel and efficient catalyst for the Knoevenagel condensation of aldehydes with acidic methylene compounds such as ethyl cyanoacetate and malononitrile to afford substituted olefins. The reaction proceeds smoothly under mild and solvent-free conditions and the products are obtained in excellent yields with an E-geometry. This method is applicable for

  三苯基膦 (TPP) 已被用作一种新型有效的催化剂，用于醛与酸性亚甲基化合物（如氰乙酸乙酯和丙二腈）的 Knoevenagel 缩合反应，得到取代的烯烃。该反应在温和且无溶剂的条件下顺利进行，产物以极好的收率获得，具有 E 几何。该方法适用于多种醛，包括芳香族、脂肪族和杂环底物。微波辐射已被用于提高反应速率和提高产率。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Synthesis and characterization of sulfamic acid supported on Fe₃ O₄ nanoparticles: A green, versatile and magnetically separable acidic catalyst for oxidation reactions and Knoevenagel condensation
  作者：Lotfi Shiri、Hojatollah Narimani、Mosstafa Kazemi

  DOI：10.1002/aoc.3927

  日期：2018.1

  Sulfamic acid immobilized on diethylenetriamine functionalized Fe3O4 nanoparticles (SA‐DETA‐Fe3O4) was successfully prepared and characterized by X‐ray diffraction (XRD), Fourier transform infrared spectroscopy (FT‐IR), vibrating sample magnetometer (VSM), thermo gravimetric analysis (TGA), X‐Ray diffraction (XRD) and scanning electron microscopy (SEM). The sulfamic acid was found as a magnetically

  成功制备了固定在二亚乙基三胺官能化的Fe 3 O 4纳米颗粒（SA-DETA-Fe 3 O 4）上的氨基磺酸，并通过X射线衍射（XRD），傅立叶变换红外光谱（FT-IR），振动样品磁力计（VSM）对其进行了表征。 ），热重分析（TGA），X射线衍射（XRD）和扫描电子显微镜（SEM）。发现氨基磺酸是用于氧化偶联的硫醇，硫化物的氧化的可磁分离和高活性的催化剂。此外，SA-DETA-Fe 3 O 4在芳族醛与活性亚甲基化合物（丙二腈和氰基乙酸乙酯）的Knoevenagel缩合反应中具有较高的催化活性。可以通过简单的磁分离容易地回收纳米固体催化剂，并在不降低催化活性的情况下重复使用许多循环。
• A Simple, Efficient and Green Procedure for Knoevenagel Condensation in Water or under Solvent-free Conditions
  作者：Ya-Qin Yu、Zhong-Liang Wang

  DOI：10.1002/jccs.201200391

  日期：2013.3

  1,4‐Diazabicyclo[2.2.2]octane was used as an efficient catalyst in the Knoevenagel condensation reaction of various kinds of aromatic/aliphatic/heterocyclic/αβ‐unsaturated aldehydes and ketones with active methylene compounds. This is a convenient and rapid method for Knoevenagel condensation, which affords the corresponding substituted electrophilic alkenes in excellent yields. The reaction condition

  1,4-二氮杂双环[2.2.2]辛烷被用作各种芳族/脂肪族/杂环/αβ-不饱和醛和酮与活性亚甲基化合物的Knoevenagel缩合反应的有效催化剂。这是用于Knoevenagel缩合的一种方便快捷的方法，该方法以极高的收率提供了相应的取代的亲电子烯烃。反应条件温和并且该方法操作简单。仅检测到电子异构体的产物无需纯化。使用水作为反应介质使该方法对环境无害。催化剂可以循环使用六次而不会损失活性。
• Transition metal polyhydrides-catalyzed addition of activated nitriles to aldehydes and ketones via Knoevenagel condensation
  作者：Yingrui Lin、Xianchao Zhu、Min Xiang

  DOI：10.1016/0022-328x(93)80087-r

  日期：1993.4

  Transition metal polyhydrides and dihydrogen complexes catalyze Knoevenagel addition of cyanoacetate to aldehydes and ketones under neutral and mild conditions, the adducts undergo dehydration to give substituted (E)-2-cyano-α,β-unsaturated esters exclusively.

  在中性和温和条件下，过渡金属多羟基化合物和二氢配合物催化氰基乙酸的氰基乙酸加成到醛和酮上，加合物脱水后仅得到取代的（E）-2-氰基-α，β-不饱和酯。
• The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
  作者：Kavita Jain、Saikat Chaudhuri、Kuntal Pal、Kalpataru Das

  DOI：10.1039/c8nj04219e

  日期：——

  organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.

  使用奎宁作为有机催化剂，可以开发出活性亚甲基化合物与芳族羰基化合物之间的Knoevenagel缩合反应，从而以极高的收率（最高90％）提供各种亲电子烯烃。在催化量的奎宁（15mol％）的存在下，反应在室温（RT）下在无溶剂条件下进行。在这种绿色方法中，有机催化剂被回收并循环使用多达四个周期，而活性没有明显下降。

表征谱图