(R)-(+)-4-butyl-2-pyrrolidinone | 210585-79-8

• 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-butyl-2-pyrrolidinone
• 英文别名: (R)-4-Butylpyrrolidin-2-one；(4R)-4-butylpyrrolidin-2-one
• CAS: 210585-79-8
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: XERCUZVKEPHPQL-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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-butyl-2-pyrrolidinone 在 盐酸 作用下， 以 水 为溶剂， 生成 (R)-(-)-3-(aminomethyl)heptanoic 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：

  (R)-4-butyl-1-(4-methoxyphenyl)-2-pyrrolidinone 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以79%的产率得到(R)-(+)-4-butyl-2-pyrrolidinone
  参考文献：
  名称：

  Steric and Electronic Influences on the Diastereoselectivity of the Rh₂(OAc)₄-Catalyzed C−H Insertion in Chiral Ester Diazoanilides:  Synthesis of Chiral, Nonracemic 4-Substituted 2-Pyrrolidinones

  摘要：

  A series of N-substituted N-(4-methoxyphenyl)-alpha-(alkoxycarbonyl)-alpha-diazoacetanilides, 10 and ent-10, wherein the alkoxy unit is a chiral auxiliary group [(-)-7 or (+)-8)], was prepared. The Rh-2(OAc)(4)-catalyzed intramolecular C-H insertion reaction of 10 and ent-10, under optimized reaction conditions, was investigated as a route for the preparation of chiral, nonracemic 4-substituted 2-pyrrolidinones. The cyclization reaction led only to 2-pyrrolidinone and 2-azetidinone products; the former products were obtained as major and, in a few cases, as exclusive products. The type and nature of the N-substituent in 10 or ent-10 was found to govern the diastereoselectivity of the reaction. With N-alkyl groups, steric effects play an important role in determining the diastereoselectivity of the reaction. However, with N-arylethyl substituents, electronic effects transmitted by the aryl substituents influenced the diastereoselectivity of the C-H insertion reaction. Specifically, electron-donating substituents were found to markedly attenuate the diastereoselectivity of the reaction. The diastereoselectivity of the reaction ranged from moderate to high (37-98%). A transition-state model to explain the observed diastereoselectivity is provided. The synthetic utility of the method is demonstrated by the stereoselective synthesis of the medicinally important, unnatural amino acid trans-4-cyclohexyl-L-proline 23.

  DOI：

  10.1021/jo971540q

文献信息

• Peptide deformylase inhibitors
  申请人：——

  公开号：US20040077856A1

  公开（公告）日：2004-04-22

  PDF inhibitors and novel methods for their use are provided.

  提供了PDF抑制剂及其使用的新方法。
• Peptide Deformylase Inhibitors
  申请人：Aubart M. Kelly

  公开号：US20070155792A1

  公开（公告）日：2007-07-05

  PDF inhibitors and novel methods for their use are provided.

  提供了PDF抑制剂和其新型使用方法。
• The synthesis of aracemic 4-substituted pyrrolidinones and 3-substituted pyrrolidines. An asymmetric synthesis of (-)-rolipram
  作者：A. I. Meyers、Lawrence Snyder

  DOI：10.1021/jo00053a012

  日期：1993.1

  Conjugate additions of RCuCNLi to the chiral alpha,beta-unsaturated lactam 4 gives almost exclusive exo addition-a reversal in stereochemistry when cuprates were added to chiral lactam 1. The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage. The chemical yields as well as the enantiomeric purity were very high for this process. As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield. Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11. Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.
• PEPTIDE DEFORMYLASE INHIBITORS
  申请人：SmithKline Beecham Corporation

  公开号：EP1363623A2

  公开（公告）日：2003-11-26
• EP1363623A4
  申请人：——

  公开号：EP1363623A4

  公开（公告）日：2004-03-31