ethyl α-(2,4-dinitrophenyl)-α-methylacetoacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl α-(2,4-dinitrophenyl)-α-methylacetoacetate
• 英文别名: Ethyl 2-(2,4-dinitrophenyl)-2-methyl-3-oxobutanoate
• 化学式: C₁₃H₁₄N₂O₇
• 分子量: 310.263
• InChiKey: FUWMYHHRQWFGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 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：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 1-氯-2,4-二硝基苯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 ethyl α-(2,4-dinitrophenyl)-α-methylacetoacetate
  参考文献：
  名称：

  Transacylation of α-Aryl-β-keto Esters

  摘要：

  The acyl group of an alpha-aryl-beta-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.

  DOI：

  10.1021/jo0344642

文献信息

• Transacylation of α-Aryl-β-keto Esters
  作者：Nagatoshi Nishiwaki、Daisei Nishida、Tetsuya Ohnishi、Fumie Hidaka、Satoru Shimizu、Mina Tamura、Kazushige Hori、Yasuo Tohda、Masahiro Ariga

  DOI：10.1021/jo0344642

  日期：2003.10.1

  The acyl group of an alpha-aryl-beta-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.