2-氰基-3-(2-甲氧基苯基)丙酸乙酯 | 100372-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-氰基-3-(2-甲氧基苯基)丙酸乙酯
• 英文名称: ethyl 2-cyano-3-(2-methoxyphenyl)propanoate
• 英文别名: Ethyl 2-cyano-3-(2-methoxyphenyl)propanoate
• CAS: 100372-58-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: DCYCGIPEPUVABU-UHFFFAOYSA-N

物化性质

• 沸点：
  165-170 °C(Press: 0.2 Torr)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-cyano-3-(2-methoxyphenyl)acrylic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以65%的产率得到2-氰基-3-(2-甲氧基苯基)丙酸乙酯
  参考文献：
  名称：

  3-亚芳基丙二酸衍生物与三乙胺和其他胺的反应；意外的减少和黑胶

  摘要：

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用

  DOI：

  10.1016/j.tet.2016.03.097

文献信息

• One-Pot Approach for C-C Bond Formation through Ruthenium-Amido Complex Catalyzed Tandem Aldol Reaction/Hydrogenation
  作者：Hong Liu、Haifeng Sun、Deju Ye、Hualiang Jiang、Kaixian Chen

  DOI：10.1055/s-0029-1218815

  日期：2010.8

  efficient approach was developed for the α-alkylation of various nitriles with carbonyl compounds using ruthenium-amido complex catalyst 1. The C-C bond was formed through aldol reaction followed by hydrogenation with triethylamine-formic acid (TEAF) and 1. Moderate to high yields were obtained, and a variety of functional groups were tolerated, including nitro and chloro groups, and a furan ring. ruthenium-amido

  开发了一种一锅新颖有效的方法，使用钌-酰胺基络合物催化剂1将各种腈与羰基化合物进行α-烷基化。CC键通过醛醇缩合反应形成，然后用三乙胺-甲酸（TEAF）和1氢化。获得了中等至高收率，并且容许各种官能团，包括硝基和氯基团以及呋喃环。 钌-酰胺基络合物-串联反应-羟醛反应-氢化-CC键
• Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives—demethylation, reduction and vinylogation
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tetlet.2015.01.148

  日期：2015.3

  3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also. (C) 2015 Elsevier Ltd. All rights reserved.
• Overturning Established Chemoselectivities: Selective Reduction of Arenes over Malonates and Cyanoacetates by Photoactivated Organic Electron Donors
  作者：Eswararao Doni、Bhaskar Mondal、Steven O’Sullivan、Tell Tuttle、John A. Murphy

  DOI：10.1021/ja4050168

  日期：2013.7.31

  The prevalence of metal-based reducing reagents, including metals, metal complexes, and metal salts, has produced an empirical order of reactivity that governs our approach to chemical synthesis. However, this reactivity may be influenced by stabilization of transition states, intermediates, and products through substrate metal bonding. This article reports that in the absence of such stabilizing interactions, established chemoselectivities can be overthrown. Thus, photoactivation of the recently developed neutral organic superelectron donor 5 selectively reduces alkyl-substituted benzene rings in the presence of activated esters and nitriles, in direct contrast to metal-based reductions, opening a new perspective on reactivity. The altered outcomes arising from the organic electron donors are attributed to selective interactions between the neutral organic donors and the arene rings of the substrates.
• Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; unexpected reductions and vinylogations
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tet.2016.03.097

  日期：2016.6

  Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用