4-氰基-2-乙基-2-(4-硝基苯基)丁酸甲酯 | 192927-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氰基-2-乙基-2-(4-硝基苯基)丁酸甲酯
• 英文名称: methyl 4-cyano-2-ethyl-2-(4-nitrophenyl)butanoate
• CAS: 192927-32-5
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: XHOIVBNLJMZOKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  93.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-氰基-2-乙基-2-(4-硝基苯基)丁酸甲酯 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 48.25h， 生成 4-(4-nitrophenyl)hexanonitrile
  参考文献：
  名称：

  Resolution of 4-cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (aminoglutethimide1)

  摘要：

  Using (R)- or (S)-1-phenylethylamine as a resolving agent, (R)- and (S)-4-cyano-4-(4-nitrophenyl)hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)- and (S)-aminoglutethimide of high (>99% ee) enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3-ethylpiperidine-2, 6-dione was solved by X-ray single crystal analysis thus establishing the (R)-configuration of the dextrorotatory aminoglutethimide. Attempted resolution of the other precursor of aminoglutethimide, 4cyano-2-ethyl(4-nitrophenyl)butanoic acid with (S)-1-phenylethylamine led to the formation of the double salt. Its crystal structure was elucidated by X-ray crystallographic analysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00464-x
• 作为产物：
  描述：

  2-(4-硝基苯基)丁酸 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 4-氰基-2-乙基-2-(4-硝基苯基)丁酸甲酯
  参考文献：
  名称：

  Resolution of 4-cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (aminoglutethimide1)

  摘要：

  Using (R)- or (S)-1-phenylethylamine as a resolving agent, (R)- and (S)-4-cyano-4-(4-nitrophenyl)hexanoic acids have been isolated. Cyclization of each enantiomer, followed by reduction of the nitro group, afforded (R)- and (S)-aminoglutethimide of high (>99% ee) enantiomeric purity, respectively. The absolute configuration of (R)-(+)-3-(4-nitrophenyl)-3-ethylpiperidine-2, 6-dione was solved by X-ray single crystal analysis thus establishing the (R)-configuration of the dextrorotatory aminoglutethimide. Attempted resolution of the other precursor of aminoglutethimide, 4cyano-2-ethyl(4-nitrophenyl)butanoic acid with (S)-1-phenylethylamine led to the formation of the double salt. Its crystal structure was elucidated by X-ray crystallographic analysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00464-x