2-甲基-2-(2-甲氧基苯基)氰基乙酸乙酯 | 1008731-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-甲基-2-(2-甲氧基苯基)氰基乙酸乙酯
• 英文名称: ethyl 2-methyl-2-(2-methoxyphenyl)cyanoacetate
• 英文别名: ethyl 2-cyano-2-(2-methoxyphenyl)propionate；Ethyl 2-cyano-2-(2-methoxyphenyl)propanoate
• CAS: 1008731-25-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: DZCCHNCUQVTUCP-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

• 作为产物：
  描述：

  2-碘苯甲醚 、 2-氰基丙酸乙酯 在 copper(l) iodide 、 sodium picolinate 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 36.0h， 以39%的产率得到2-甲基-2-(2-甲氧基苯基)氰基乙酸乙酯
  参考文献：
  名称：

  Synthesis of 2-alkyl-2-arylcyanoacetates via CuI/sodium picolinate-catalyzed direct arylation of α-substituted cyanoacetates

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2013.05.057

文献信息

• Palladium-Catalyzed One-Pot Synthesis of 2-Alkyl-2-arylcyanoacetates
  作者：Xiang Wang、Anil Guram、Emilio Bunel、Guo-Qiang Cao、Jennifer R. Allen、Margaret M. Faul

  DOI：10.1021/jo7024338

  日期：2008.2.1

  [GRAPHICS]A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)(2)/DPPF (DPPF = 1,1'-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.
• US5532386A
  申请人：——

  公开号：US5532386A

  公开（公告）日：1996-07-02
• 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.