4-氰基-4-(4-硝基苯基)己酸乙酯 | 194422-71-4

• 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-4-(4-硝基苯基)己酸乙酯
• 英文名称: ethyl 4-cyano-4-(4-nitrophenyl)hexanoate
• CAS: 194422-71-4
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: UHICSCQSISUZEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氰基-4-(4-硝基苯基)己酸乙酯 在 盐酸 、 5%-palladium/activated carbon 、 水 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 (R)-(+)-氨鲁米特
  参考文献：
  名称：

  Production of (R)-Aminoglutethimide:  A New Route from 1-Chloro-4-nitrobenzene

  摘要：

  The development of a short, safe and enantioselective route for the preparation of (R)-aminoglutethimide is described, The process was designed for economic large-scale manufacture of the bulk drug substance to acceptable quality standards, to allow clinical evaluation of the single enantiomer over the existing racemate. (R)-Aminoglutethimide was prepared from 1-chloro-4-nitrobenzene using a six-stage synthetic sequence, via chemoresolution of key intermediate racemic 4-cyano-4-(4-nitrophenyl)hexanoic acid using (-)-cinchonidine, The process allowed for preparation of several kilograms of the precursor (R)-nitroglutethimide, to cGMP at pilot-plant scale, along with demonstration of the find hydrogenation step to (R)-amino-glutethimide in the laboratory, This route avoids the problems of hazardous nitration technology, and therefore regio-isomer contamination of the product, associated with other procedures. The resolution chemistry described represents an improvement on literature procedures, Optimisation of the asymmetric Michael addition offers an attractive alternative approach.

  DOI：

  10.1021/op9900075
• 作为产物：
  描述：

  2-(4-硝基苯基)氰基乙酸甲酯 在 水 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 Petroleum ether 为溶剂， 反应 14.5h， 生成 4-氰基-4-(4-硝基苯基)己酸乙酯
  参考文献：
  名称：

  Production of (R)-Aminoglutethimide:  A New Route from 1-Chloro-4-nitrobenzene

  摘要：

  The development of a short, safe and enantioselective route for the preparation of (R)-aminoglutethimide is described, The process was designed for economic large-scale manufacture of the bulk drug substance to acceptable quality standards, to allow clinical evaluation of the single enantiomer over the existing racemate. (R)-Aminoglutethimide was prepared from 1-chloro-4-nitrobenzene using a six-stage synthetic sequence, via chemoresolution of key intermediate racemic 4-cyano-4-(4-nitrophenyl)hexanoic acid using (-)-cinchonidine, The process allowed for preparation of several kilograms of the precursor (R)-nitroglutethimide, to cGMP at pilot-plant scale, along with demonstration of the find hydrogenation step to (R)-amino-glutethimide in the laboratory, This route avoids the problems of hazardous nitration technology, and therefore regio-isomer contamination of the product, associated with other procedures. The resolution chemistry described represents an improvement on literature procedures, Optimisation of the asymmetric Michael addition offers an attractive alternative approach.

  DOI：

  10.1021/op9900075

文献信息

• CHIRAL COMPOUNDS AND THEIR RESOLUTION
  申请人：Chiroscience Limited

  公开号：EP0763023A1

  公开（公告）日：1997-03-19
• RACEMISATION OF QUATERNARY CHIRAL CENTERS
  申请人：Darwin Discovery Limited

  公开号：EP0880497A1

  公开（公告）日：1998-12-02
• US5661014A
  申请人：——

  公开号：US5661014A

  公开（公告）日：1997-08-26
• US5821369A
  申请人：——

  公开号：US5821369A

  公开（公告）日：1998-10-13
• [EN] CHIRAL COMPOUNDS AND THEIR RESOLUTION<br/>[FR] COMPOSES CHIRAUX ET LEUR RESOLUTION
  申请人：CHIROSCIENCE LIMITED

  公开号：WO1995032947A1

  公开（公告）日：1995-12-07

  (EN) Enantiomeric glutarimides such as aminoglutethimide and rogletimide are prepared by cyclisation of a corresponding ester-nitrile which is a good substrate for biotransformation with an enantiospecific esterase.(FR) On prépare des glutarimides énantiomères tels que l'aminoglutéthimide et le roglétimide par cyclisation d'un ester-nitrile correspondant constituant un bon substrat pour la biotransformation à l'aide d'une estérase énantiospécifique.