ethyl 2-cyano-3-(2-methylphenyl)acrylate | 24393-41-7

• 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
• 英文名称: ethyl 2-cyano-3-(2-methylphenyl)acrylate
• 英文别名: (E)-ethyl 2-cyano-3-o-tolylacrylate；ethyl (E)-2-cyano-3-(o-tolyl)acrylate；(E)-ethyl 3-(2-methylphenyl)-2-cyanoacrylate；2-<2-Methyl-benzyliden>-cyanessigsaeure-aethylester；trans-2-Cyan-3-o-tolyl-acrylsaeure-ethylester；Ethyl 2-cyano-3-(2-methylphenyl)prop-2-enoate；ethyl (E)-2-cyano-3-(2-methylphenyl)prop-2-enoate
• CAS: 24393-41-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: FPBJDRRJLHQBJS-XYOKQWHBSA-N

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

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-3-(2-methylphenyl)acrylate 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 74.08h， 生成 3-(2-methylphenyl)pentan-1,5-dioic 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-溴苯甲醛乙烯醛 在 四氢吡咯 、 盐酸 、 magnesium 、 溶剂黄146 、 丙酮 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 ethyl 2-cyano-3-(2-methylphenyl)acrylate
  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

• Tri-lacunary polyoxometalates of Na8H[PW9O34] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives
  作者：Shen Zhao、Yang Chen、Yu-Fei Song

  DOI：10.1016/j.apcata.2014.01.017

  日期：2014.4

  development of tri-lacunary polyoxometalates (POMs) of Na8H[A-PW9O34]·7H2O and Na8H[B-PW9O34]·19H2O (Na-A-PW9 and Na-B-PW9) as highly selective and efficient heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation of various aldehydes and ketones and the synthesis of benzoxazole derivatives at 25 °C under mild conditions. Since both Na-A-PW9 and Na-B-PW9 display no characteristic porosity

  我们报道首次开发三钠的多金属氧酸盐-lacunary（多金属氧酸盐）8 H [A-PW 9 ö 34 ]·7H 2 O和Na 8 H [B-PW 9 ö 34 ]·19H 2 O（钠-A-PW 9和Na-B-PW 9）是高选择性和高效的均相Lewis碱催化剂，用于Knoevenagel缩合，各种醛和酮的氰基硅烷化以及在25°C下于温和条件下合成苯并恶唑衍生物。由于Na-A-PW 9和Na-B-PW 9由于没有显示出特征性的孔隙率，建议催化反应不仅在表面和界面上进行，而且在本体相中进行。催化剂可以容易地回收并重复使用至少六次而不会明显降低催化活性，并且催化剂的结构在循环后保持不变。Na-A-PW 9和Na-B-PW 9的多相催化剂易于制备，高效且可重复使用，具有进一步应用的巨大潜力。
• Classical Keggin Intercalated into Layered Double Hydroxides: Facile Preparation and Catalytic Efficiency in Knoevenagel Condensation Reactions
  作者：Yueqing Jia、Yanjun Fang、Yingkui Zhang、Haralampos N. Miras、Yu-Fei Song

  DOI：10.1002/chem.201501953

  日期：2015.10.12

  Knoevenagel condensation reactions of various aldehydes and ketones with Z‐CH2‐Z′ type substrates (ethyl cyanoacetate and malononitrile) at 60 °C in mixed solvents (V2‐propanol:Vwater=2:1) demonstrated highly efficient catalytic activity. The synergistic effect between the acidic and basic sites of the Mg3Al‐PW12 composite proved to be crucial for the efficiency of the condensation reactions. Additionally

  多金属氧酸盐（POM）插层层状双氢氧化物（LDH）复合材料家族对于设计具有多种应用的功能性材料具有广阔的前景。众所周知，由于空间和几何限制，传统的离子交换方法很难将[PW 12 O 40 ] 3−（PW 12）的经典Keggin多金属氧酸盐（POM）插入层状双氢氧化物（LDHs）中。在本文中，镁这样的插层化合物0.73的Al 0.22（OH）2 [PW 12 ø 40 ] 0.04 ⋅0.98ħ 2 O（Mg的3通过采用自发絮凝方法已成功获得了Al-PW 12）。Mg 3 Al-PW 12已通过多种方法（XRD，SEM，TEM，XPS，EDX，XPS，FT-IR，NMR，BET）进行了全面表征。Mg 3 Al-PW 12的XRD图谱通常在（003）衍射峰附近没有观察到杂质相。中的Mg的后续应用3的Al-PW 12在各种醛和酮与Z-CH Knoevenagel缩合反应催化剂2 -Z'，在60
• Layered double hydroxide anchored ionic liquids as amphiphilic heterogeneous catalysts for the Knoevenagel condensation reaction
  作者：Tengfei Li、Wei Zhang、Wei Chen、Haralampos N. Miras、Yu-Fei Song

  DOI：10.1039/c7dt03665e

  日期：——

  attention has been dedicated to the development of heterogeneous base catalysts providing a green and sustainable process in benign aqueous media. Herein, the ionic liquid modified layered double hydroxide (LDH) based catalysts of LDH-IL-Cn (n = 4, 8, 12) were prepared by adopting an exfoliation/assembly strategy, in which the ionic liquids (ILs) were covalently anchored onto the surface of LDH layers. The

  近年来，人们一直致力于开发在良性水性介质中提供绿色和可持续工艺的非均相碱催化剂。在此，通过采用剥落/组装策略制备了LDH-IL-C n（n = 4、8、12）的离子液体改性层状双氢氧化物（LDH）基催化剂，其中离子液体（ILs）是共价的固定在LDH层的表面上。通过FT-IR，固态13 C NMR，29 Si CP / MAS NMR，27 Al-MAS NMR，XRD，TG-DTA，BET，XPS，SEM，CO 2-表征所得的LDH-IL-C n。 TPD，接触角实验等。在室温下，LDH-IL-C12在H 2 O中对各种醛与氰基乙酸乙酯/丙二腈的Knoevenagel缩合反应的催化性能显示出优异的收率和选择性。而且，LDH-IL-C12的碱催化剂可以容易地再循环和再使用至少5次，而不会降低其催化效率。放大实验表明，该催化剂保留了其效率和坚固性。
• Amino Acid Amide based Ionic Liquid as an Efficient Organo-Catalyst for Solvent-free Knoevenagel Condensation at Room Temperature
  作者：Pralhad A. Burate、Balasaheb R. Javle、Pranjal H. Desale、Anil K. Kinage

  DOI：10.1007/s10562-019-02840-5

  日期：2019.9

  Ionic liquids of amino acid amide were synthesized and used as an efficient catalyst for solvent-free Knoevenagel condensation. Synthesized ionic liquids are an environmentally benign, inexpensive, metal free and plays the dual role of solvent as well as an efficient catalyst for Knoevenagel condensation. A wide range of aliphatic, aromatic and heteroaromatic aldehydes easily undergo condensation with

  合成了氨基酸酰胺离子液体，并将其用作无溶剂 Knoevenagel 缩合的有效催化剂。合成的离子液体是一种环境友好、价格低廉、不含金属的物质，既是溶剂又是 Knoevenagel 缩合的有效催化剂。多种脂肪族、芳香族和杂芳香族醛很容易与丙二腈和氰基乙酸乙酯缩合。该反应在室温下进行，无需使用任何有机溶剂，反应速度非常快，收率非常好。此外，该催化剂易于分离和回收而不会损失活性。Graphic Abstract
• Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes
  作者：Sang-Yun Kim、Pan-Suk Kwon、Tae-Woo Kwon、Sung-Kee Chung、Young-Tae Chang

  DOI：10.1080/00397919708003323

  日期：1997.2

  Abstract The reaction rate of Knoevenagel condensation can be dramatically enhanced by irradiating the reaction mixture containing ethyl cyanoacetate, an aldehyde, P2O5, piperidine, and chlorobenzene with a commercial microwave oven. A number of Knoevenagel condensation products were prepared in good yields in very short reaction times (2-15min) under the microwave irradiation.

  摘要 用商用微波炉照射含有氰乙酸乙酯、醛、P2O5、哌啶和氯苯的反应混合物，可以显着提高Knoevenagel缩合的反应速率。在微波辐射下，在非常短的反应时间（2-15 分钟）内以良好的收率制备了许多 Knoevenagel 缩合产物。

表征谱图