3-cyanopentane-1,5-dioic acid diethyl ester | 104296-80-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-cyanopentane-1,5-dioic acid diethyl ester
• 英文别名: β-Cyan-glutarsaeure-diethylestser；3-Cyano-pentanedioic acid diethyl ester；diethyl 3-cyanopentanedioate
• CAS: 104296-80-2
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: AGAFHSVNJCPMTR-UHFFFAOYSA-N

物化性质

• 沸点：
  141-144 °C(Press: 2 Torr)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-cyanopentane-1,5-dioic acid diethyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  [EN] MANUFACTURING PROCESS FOR (S)-PREGABALIN
  [FR] PROCÉDÉ DE FABRICATION DE LA (S)-PRÉGABALINE

  摘要：

  本发明涉及一种新型制造工艺和新型中间体，可用于合成通式（I）的药物活性化合物，用于治疗癫痫、神经病性疼痛、焦虑和社交恐惧症。该发明描述了从通式（IV）的手性吡咯烷-2-酮制备对映纯的（S）-普瑞巴林的方法。

  公开号：

  WO2012059830A1
• 作为产物：
  描述：

  triethyl 2-cyano-1,2,3-propanetricarboxylate 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以83%的产率得到3-cyanopentane-1,5-dioic acid diethyl ester
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357

文献信息

• Henecka,H. et al., Angewandte Chemie, 1960, vol. 72, p. 960 - 963
  作者：Henecka,H. et al.

  DOI：——

  日期：——
• SIZOV, A. YU.;DOMBROVSKIJ, V. A.;YANOVSKAYA, L. A., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1073-1079
  作者：SIZOV, A. YU.、DOMBROVSKIJ, V. A.、YANOVSKAYA, L. A.

  DOI：——

  日期：——
• US8466297B2
  申请人：——

  公开号：US8466297B2

  公开（公告）日：2013-06-18
• Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions
  作者：A. Yu. Sizov、V. A. Dombrovskii、L. A. Yanovskaya

  DOI：10.1007/bf00961357

  日期：1991.5

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.
• [EN] MANUFACTURING PROCESS FOR (S)-PREGABALIN<br/>[FR] PROCÉDÉ DE FABRICATION DE LA (S)-PRÉGABALINE
  申请人：DRUG PROCESS LICENSING ASS LLC

  公开号：WO2012059830A1

  公开（公告）日：2012-05-10

  The present invention relates to a novel manufacturing process and novel intermediates useful in the synthesis of pharmaceutically active compounds of general formula (I) used for treatment of epilepsy, neuropathic pain, anxiety and social phobia. The invention describes preparation of enantiomerically pure (S)-Pregabalin from chiral pyrrolidin-2-one of formula (IV).

  本发明涉及一种新型制造工艺和新型中间体，可用于合成通式（I）的药物活性化合物，用于治疗癫痫、神经病性疼痛、焦虑和社交恐惧症。该发明描述了从通式（IV）的手性吡咯烷-2-酮制备对映纯的（S）-普瑞巴林的方法。