(R)-(+)-4-pentyl-2-pyrrolidinone | 1039497-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-(+)-4-pentyl-2-pyrrolidinone
• 英文别名: (4R)-4-pentylpyrrolidin-2-one
• CAS: 1039497-73-8
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: MITYOFHEBMHYOJ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-4-pentyl-2-pyrrolidinone 在 盐酸 作用下， 以 水 为溶剂， 生成 (R)-(-)-3-(aminomethyl)octanoic acid hydrochloride
  参考文献：
  名称：

  A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

  摘要：

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.014
• 作为产物：
  描述：

  ethyl (R)-(-)-3-(nitromethyl)octanoate 在 镍 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 以72%的产率得到(R)-(+)-4-pentyl-2-pyrrolidinone
  参考文献：
  名称：

  A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin

  摘要：

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.014

文献信息

• [EN] METHOD OF PREPARING OPTICALLY ACTIVE 4-ARYL-2-PYRROLIDINONES
  申请人：SCHERING AKTIENGESELLSCHAFT BERLIN UND BERGKAMEN

  公开号：WO1992006077A1

  公开（公告）日：1992-04-16

  (DE) Stereoselektives Verfahren zur Herstellung von (4R)- oder (4S)-4-Aryl-2-pyrrolidinonen der Formel (I), worin R1 Wasserstoff oder einen gegebenenfalls mit einem Sauerstoffatom unterbrochenen Kohlenwasserstoffrest mit bis zu 7 Kohlenstoffatomen und R2 eine C1-4-Alkylgruppe bedeutet, sowie Zwischenprodukte und das stereoselektive Verfahren zur Herstellung der optisch aktiven Zwischenverbindungen.(EN) Disclosed is a stereo-selective method for the preparation of (4R)- or (4S)-4-aryl-2-pyrrolidinones of formula (I), in which R1 is hydrogen or a hydrocarbon group with up to 7 carbon atoms which may contain an oxygen atom in the carbon chain and R2 is a C1-4 alkyl group, as well as intermediates and a stereo-selective method for the preparation of the optically active intermediate compounds.(FR) Procédé stéréosélectif pour la fabrication de (4R)- ou (4S)-4-Aryle-2-pyrrolidinones de formule (I) où R1 représente l'oxygène ou, le cas échéant, un radical d'hydrocarbure interrompu par un atome d'oxygène et ayant jusqu'à 7 atomes de carbone, et où R2 représente un groupe alkyle C1-4. L'invention concerne également des produits intermédiaires et le procédé stéréosélectif pour la fabrication des produits intermédiaires optiquement actifs.

  （DE）一种用于合成（4R）或（4S）-4-aryl-2-pyrrolidinones（化学式为（I））的立体选择方法，其中R1是氢或可能含一个氧原子的一断链或带有不超过7个碳原子的碳链的水化物 rests，R2是一个C1-4 羟基团，以及中间产物和用于合成光学活性中间化合物的立体选择方法。 （EN）一种用于合成（4R）或（4S）-4-aryl-2-pyrrolidinones（化学式为（I））的立体选择方法，其中R1是氢或可能含一个氧原子的一段链或带有不超过7个碳原子的碳链的水化物 rests，R2是C1-4 群，以及用于合成光学活性中间化合物的立体选择方法。 （FR）一种用于合成（4R）或（4S）-4-Aryle-2-pyrrolidinones（化学式为（I））的立体选择方法，其中R1是一氧化氢或氢或可能含一个氧原子的一段链或带有不超过7个碳原子的碳链的水化物 rests，R2是C1-4 群。该发明还包括中间产物和用于合成光学活性中间化合物的立体选择方法。
• VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEN 4-ARYL-2-PYRROLIDINONEN
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0504351A1

  公开（公告）日：1992-09-23
• US5298628A
  申请人：——

  公开号：US5298628A

  公开（公告）日：1994-03-29
• A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin
  作者：Fulvia Felluga、Giuliana Pitacco、Ennio Valentin、Cesare Daniele Venneri

  DOI：10.1016/j.tetasy.2008.03.014

  日期：2008.5

  Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative (S)-(+)-7d, which underwent conversion into its corresponding succinic acid derivative (S)-(-)-8d in buffered solution. The absolute configurations of the main Compounds of interest involved are given, together with their CD spectra. (C) 2008 Elsevier Ltd. All rights reserved.