ethyl 2-cyano-2-(4-methoxyphenyl)propionate | 133857-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-cyano-2-(4-methoxyphenyl)propionate
• 英文别名: Ethyl 2-cyano-2-(4-methoxyphenyl)propanoate
• CAS: 133857-58-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: SEFSYPPNWGQDMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  ethyl 2-cyano-2-(4-methoxyphenyl)propionate 在 ammonium hydroxide 作用下， 生成 2-cyano-2-(4-methoxy-phenyl)-propionic acid amide
  参考文献：
  名称：

  Para-Methoxyphenylmalonic Acid and its Derivatives¹

  摘要：

  DOI：

  10.1021/ja01289a032
• 作为产物：
  描述：

  对甲氧基苯乙腈 在 乙醚 、 sodium ethanolate 、 sodium 作用下， 生成 ethyl 2-cyano-2-(4-methoxyphenyl)propionate
  参考文献：
  名称：

  Para-Methoxyphenylmalonic Acid and its Derivatives¹

  摘要：

  DOI：

  10.1021/ja01289a032

文献信息

• <i>tert</i>-Butoxide-Mediated Arylation of 2-Substituted Cyanoacetates with Diaryliodonium Salts
  作者：Xiaofei Qian、Jianwei Han、Limin Wang

  DOI：10.1002/adsc.201501013

  日期：2016.3.17

  A transition metal‐free direct arylation of 2‐substituted cyanoacetates with diaryliodonium salts was developed. With this approach, a wide range of α‐tolunitrile derivatives has been synthesized in good to excellent yields of 45–92%. Furthermore, the practicability of this approach is further manifested in the synthesis of a related bioactive agent of glutarimide.

  开发了无过渡金属的2-取代氰基乙酸盐与二芳基碘鎓盐的直接芳基化反应。通过这种方法，已经合成了范围广泛的α-甲苯二酚衍生物，收率高达45％至92％。此外，该方法的实用性在戊二酰亚胺的相关生物活性剂的合成中得到进一步证明。
• Copper-Promoted Reaction of Aryl Iodides with Activated Methine Compounds
  作者：Sommai Pivsa-Art、Yuka Fukui、Masahiro Miura、Masakatsu Nomura

  DOI：10.1246/bcsj.69.2039

  日期：1996.7

  compound, diethyl acetamidomalonate, can efficiently proceed in the presence of CuI and NaH in DMSO to give diethyl acetamido(aryl)malonates, which may be useful precursors for α-arylglycines, in good yields. Although the reaction with another methine substrate, ethyl 2-cyanopropionate, also affords the expected coupling products, no substitution products are obtained in the case of diethyl methylmalonate

  芳基碘化物与活化的次甲基化合物乙酰氨基丙二酸二乙酯的反应可以在 CuI 和 NaH 的 DMSO 中有效进行，得到乙酰氨基（芳基）丙二酸二乙酯，其可能是 α-芳基甘氨酸的有用前体，收率良好。尽管与另一种次甲基底物 2-氰基丙酸乙酯的反应也提供了预期的偶联产物，但在甲基丙二酸二乙酯、芳烃以及正在形成的酯的氧化偶联化合物的情况下没有获得取代产物。
• Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch
  作者：Chiara Biagini、Simone Albano、Rachele Caruso、Luigi Mandolini、José Augusto Berrocal、Stefano Di Stefano

  DOI：10.1039/c7sc04123c

  日期：——

  This work deals with the use of 2-cyano-2-arylpropanoic acids as chemical fuels for an acid–base operated molecular switch that consists of a Sauvage-type catenand composed of two identical macrocycles incorporating a phenanthroline unit. When used as a base promoter of the decarboxylation of propanoic acid derivatives, the switch undergoes large amplitude motion from the neutral catenand to a protonated

  这项工作涉及使用 2-氰基-2-芳基丙酸作为酸碱操作分子开关的化学燃料，该分子开关由一个 Sauvage 型链和两个相同的大环组成，其中包含一个菲咯啉单元。当用作丙酸衍生物脱羧的碱促进剂时，该开关经历从中性链到质子化链并再次回到中性状态的大幅度运动。决定整个过程速率的反质子转移速率受到对位取代基的显着影响，顺序为 Cl > H > CH 3 > OCH 3 ( ρ = +5.2)。因此，OCH 3完成一个完整周期所需的时间几乎是两天导数，对于 Cl 导数下降到几分钟。这些结果首次表明，分子开关的操作速率可以通过燃料结构的变化来调节。
• Synthesis of 2-alkyl-2-arylcyanoacetates via CuI/sodium picolinate-catalyzed direct arylation of α-substituted cyanoacetates
  作者：Siwei Xie、Peng Qin、Meng Li、Xiaojing Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1016/j.tetlet.2013.05.057

  日期：2013.7

  CuI/sodium picolinate-catalyzed direct arylation of alpha-substituted cyanoacetates takes place at 60 degrees C in the presence of Cs2CO3 and 4 angstrom molecular sieve, affording 2-alkyl-2-arylcyanoacetates in good to excellent yields. Both electron-rich and electronic-deficient aryl iodides, and some functionalized a-substituted cyanoacetates are compatible with the reaction conditions, thereby allowing diverse synthesis of 2-alkyl-2-arylcyanoacetates. (C) 2013 Elsevier Ltd. All rights reserved.
• Kozyrod, Robert P.; Morgan, Jacqueline; Pinhey, John T., Australian Journal of Chemistry, 1991, vol. 44, # 3, p. 369 - 376
  作者：Kozyrod, Robert P.、Morgan, Jacqueline、Pinhey, John T.

  DOI：——

  日期：——