diethyl 2-(2-ethoxybenzyl)-2-propylmalonate | 1447797-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-(2-ethoxybenzyl)-2-propylmalonate
• CAS: 1447797-38-7
• 化学式: C₁₉H₂₈O₅
• 分子量: 336.428
• InChiKey: CXESWUQLAXYOEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-ethoxybenzyl)-2-propylmalonate 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 72.0h， 以59%的产率得到丙戊酸钠杂质15
  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：

  1-溴甲基-2-乙氧基苯 、 丙基丙二酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以76%的产率得到diethyl 2-(2-ethoxybenzyl)-2-propylmalonate
  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