2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid ethyl ester | 16066-99-2

• 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: 2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid ethyl ester
• 英文别名: Ethyl 2-methyl-2-nitro-3-(4-nitrophenyl)propanoate
• CAS: 16066-99-2
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: VWQYRVSBGWWJKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid ethyl ester 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 Amberlite IR 120 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2-amino-2-methyl-3-(4-aminophenyl)propionic acid
  参考文献：
  名称：

  Synthesis of Cαα-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion

  摘要：

  The ethyl 2-nitropropionate anion was shown to react with six reductive alkylating agents to give new C-alpha alpha-unsymmctrically disubstituted nitroesters and in some cases new ethyl monosubstituted methacrylates. The C-alkylation was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the electron-withdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or TEMPO. For example, ethyl 2-methyl-2-nitro-3-p-nitrophenylpropionate was transformed in the corresponding amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00194-x
• 作为产物：
  描述：

  1-(氯甲基)-4-硝基苯 、 2-硝基丙酸乙酯 在 氧气 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 以47%的产率得到2-Methyl-2-nitro-3-(4-nitro-phenyl)-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis of Cαα-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion

  摘要：

  The ethyl 2-nitropropionate anion was shown to react with six reductive alkylating agents to give new C-alpha alpha-unsymmctrically disubstituted nitroesters and in some cases new ethyl monosubstituted methacrylates. The C-alkylation was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the electron-withdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or TEMPO. For example, ethyl 2-methyl-2-nitro-3-p-nitrophenylpropionate was transformed in the corresponding amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00194-x

文献信息

• Reaction of nitro anions with N, N-dimethyl-p-hydroxybenzylamine. New synthesis of .alpha.-methyltyrosine
  作者：Walfred S. Saari

  DOI：10.1021/jo01287a087

  日期：1967.12
• Synthesis of Cαα-unsymmetrically disubstituted nitroesters by electron transfer C-alkylation of ethyl 2-nitropropionate anion
  作者：Valérie Béraud、Patricia Perfetti、Christine Pfister、Mustapha Kaafarani、Patrice Vanelle、Michel P. Crozet

  DOI：10.1016/s0040-4020(98)00194-x

  日期：1998.5

  The ethyl 2-nitropropionate anion was shown to react with six reductive alkylating agents to give new C-alpha alpha-unsymmctrically disubstituted nitroesters and in some cases new ethyl monosubstituted methacrylates. The C-alkylation was shown to proceed by the S(RN)1 mechanism which was confirmed by the classical criteria for S(RN)1 reaction: the electron-withdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or TEMPO. For example, ethyl 2-methyl-2-nitro-3-p-nitrophenylpropionate was transformed in the corresponding amino acid. (C) 1998 Elsevier Science Ltd. All rights reserved.