2-benzyl-2-cyano-3-(4-cyanophenyl)propionic acid ethyl ester | 1447797-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-benzyl-2-cyano-3-(4-cyanophenyl)propionic acid ethyl ester
• 英文别名: Ethyl 2-benzyl-2-cyano-3-(4-cyanophenyl)propanoate；ethyl 2-benzyl-2-cyano-3-(4-cyanophenyl)propanoate
• CAS: 1447797-50-3
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: SRYGAORDDWRXIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzyl-2-cyano-3-(4-cyanophenyl)propionic acid ethyl ester 在 N,N,N',N'-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a;2',1'-c][1,4]diazepine-2,12-diamine 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 36.0h， 以75%的产率得到2-氰基-3-苯基-丙酸乙酯
  参考文献：
  名称：

  Overturning Established Chemoselectivities: Selective Reduction of Arenes over Malonates and Cyanoacetates by Photoactivated Organic Electron Donors

  摘要：

  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.

  DOI：

  10.1021/ja4050168
• 作为产物：
  描述：

  溴甲苯 、 氰乙酸乙酯 、 4-氰基苯甲醛 在 二氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 neat (no solvent) 为溶剂， 以24%的产率得到2-benzyl-2-cyano-3-(4-cyanophenyl)propionic acid ethyl ester
  参考文献：
  名称：

  碱促进了用于合成 2,2-二取代氰基乙酸乙酯的 Ramachary 还原偶联/烷基化反应的一锅无溶剂版本†

  摘要：

  开发了一种用于合成 2,2-二取代氰基乙酸乙酯的N , N-二异丙基乙胺促进的无溶剂 Ramachary 还原偶联/烷基化 (RRC/A) 反应。通过市售的醛、氰基乙酸乙酯、卤代烷和 Hantzsch 酯的 RRC/A 反应，在一锅中合成了一系列 2,2-二取代的氰基乙酸乙酯。还开发了一种无溶剂两步多组分反应，用于制备 2,2-二烷基化丙二腈和 2,2-二烷基化 4-硝基苯基乙腈。通过这些方法，所有设计的RRC/A产品都可以很容易地以良好的收率获得。

  DOI：

  10.1039/c8ra00326b

文献信息

• A base promoted one pot solvent free version of the Ramachary reductive coupling/alkylation reaction for the synthesis of 2,2-disubstituted ethyl cyanoacetates
  作者：Guangyou Jiang、Min Liu、Dongmei Fang、Ping Tan、Min Huang、Taiping Zhou、Zhenju Jiang、Zhihong Xu、Zhouyu Wang

  DOI：10.1039/c8ra00326b

  日期：——

  reductive coupling/alkylation (RRC/A) reaction for the synthesis of 2,2-disubstituted ethyl cyanoacetates has been developed. A series of 2,2-disubstituted ethyl cyanoacetates were synthesized in one pot by the RRC/A reaction of commercially available aldehydes, ethyl cyanacetates, alkyl halides and Hantzsch ester. A solvent free two step multicomponent reaction has also been developed for the preparation

  开发了一种用于合成 2,2-二取代氰基乙酸乙酯的N , N-二异丙基乙胺促进的无溶剂 Ramachary 还原偶联/烷基化 (RRC/A) 反应。通过市售的醛、氰基乙酸乙酯、卤代烷和 Hantzsch 酯的 RRC/A 反应，在一锅中合成了一系列 2,2-二取代的氰基乙酸乙酯。还开发了一种无溶剂两步多组分反应，用于制备 2,2-二烷基化丙二腈和 2,2-二烷基化 4-硝基苯基乙腈。通过这些方法，所有设计的RRC/A产品都可以很容易地以良好的收率获得。
• 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.