(3-Ethylphenyl) 2,2-dimethylpropanoate | 1204242-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (3-Ethylphenyl) 2,2-dimethylpropanoate
• 英文别名: (3-ethylphenyl) 2,2-dimethylpropanoate
• CAS: 1204242-97-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: QYYRYCJYQJNCAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 (3-Ethylphenyl) 2,2-dimethylpropanoate 在 disodium hydrogenphosphate 、 溴化铵 、 C₁₅H₂₂Br₂N₂NiO 作用下， 以88%的产率得到
  参考文献：
  名称：

  Dual Nickel/Photoredox‐Catalyzed Asymmetric Carbamoylation of Benzylic C(sp³)−H Bonds

  摘要：

  Radical‐mediated Hydrogen Atom Abstraction of Csp³−H bonds has become a powerful tool for the asymmetric functionalization of organic feedstocks. Here, we present an asymmetric synthesis of α‐aryl amides via carbamoylation of alkylarenes with isocyanates as electrophiles. The synergistic combination of a photoredox and a chiral nickel‐catalyst, enables the use of readily available and neutral reagents under mild reaction conditions and provides straightforward access to pharmacologically relevant motifs in enantiomerically pure form.

  DOI：

  10.1002/anie.202313717
• 作为产物：
  描述：

  三乙基硼 、 3-bromophenyl pivalate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以83%的产率得到(3-Ethylphenyl) 2,2-dimethylpropanoate
  参考文献：
  名称：

  在温和的非水条件下，三烷基硼烷与芳族溴化物的直接B-烷基铃木-Miyaura交叉偶联存在未掩盖的酸性或基本功能以及对碱不稳定的保护作用

  摘要：

  Abstractmagnified imageAn efficient and chemoselective palladium‐catalyzed direct B‐alkyl Suzuki–Miyaura cross‐coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non‐aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base‐labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.

  DOI：

  10.1002/adsc.200800630

文献信息

• Direct B-Alkyl Suzuki-Miyaura Cross-Coupling of Trialkyl- boranes with Aryl Bromides in the Presence of Unmasked Acidic or Basic Functions and Base-Labile Protections under Mild Non-Aqueous Conditions
  作者：Bing Wang、Hui-Xia Sun、Zhi-Hua Sun、Guo-Qiang Lin

  DOI：10.1002/adsc.200800630

  日期：2009.2

  Abstractmagnified imageAn efficient and chemoselective palladium‐catalyzed direct B‐alkyl Suzuki–Miyaura cross‐coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non‐aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base‐labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.
• Dual Nickel/Photoredox‐Catalyzed Asymmetric Carbamoylation of Benzylic C(sp³)−H Bonds
  作者：Sergio Cuesta‐Galisteo、Johannes Schörgenhumer、Cedric Hervieu、Cristina Nevado

  DOI：10.1002/anie.202313717

  日期：2024.3.18

  Radical‐mediated Hydrogen Atom Abstraction of Csp³−H bonds has become a powerful tool for the asymmetric functionalization of organic feedstocks. Here, we present an asymmetric synthesis of α‐aryl amides via carbamoylation of alkylarenes with isocyanates as electrophiles. The synergistic combination of a photoredox and a chiral nickel‐catalyst, enables the use of readily available and neutral reagents under mild reaction conditions and provides straightforward access to pharmacologically relevant motifs in enantiomerically pure form.