4-benzyl-2-pyrrolidinone | 881404-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyl-2-pyrrolidinone
• 英文别名: (S)-4-benzylpyrrolidin-2-one；2-Pyrrolidinone, 4-(phenylmethyl)-, (4S)-；(4S)-4-benzylpyrrolidin-2-one
• CAS: 881404-51-9
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: OKESWHAZOJRHIT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Methyl 3-[bis(trimethylsilyl)methyl-(3-phenylpropyl)amino]-2-diazo-3-oxopropanoate 在 ammonium cerium(IV) nitrate 、 dirhodium(II) tetrakis[N-phthaloyl-(S)-triethylalaninate] 、 sodium carbonate 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 32.5h， 生成 4-benzyl-2-pyrrolidinone
  参考文献：
  名称：

  Intramolecular asymmetric C–H insertion of N-arylalkyl, N-bis(trimethylsilyl)methyldiazoamides mediated by chiral rhodium(II) catalysts. Synthesis of (R)-β-benzyl-γ-aminobutyric acid

  摘要：

  The enantio- and site-selectivity of the intramolecular C-H insertion reactions of acyclic N-arylalkyl, N-bis(trimethylsilyl)methyl alpha-diazoacetamides, and alpha-carboalkoxy-alpha-diazoacetamides 1a-g, catalyzed by chiral Rh(II) carboxamidates and Rh(II) carboxylates were studied. In general, the reaction showed good to excellent chemoselectivity. Regio selectivity for most of the reactions was high, but was also found to be influenced by the structure of the diazo substrate and the chiral Rh(II) catalyst employed. The highest enantioselectivity for the reactions catalyzed by chiral Rh(II) carboxamidates was 69% and Rh-2(4R-MEOX)(4) was found to be the most effective. For the chiral Rh(II) carboxylate catalyzed reactions, the highest ee obtained was 75% and Rh-2(S-PTTL)(4) is the optimal catalyst. The method was applied toward the synthesis of a GABA analogue, (R)-beta-benzyl-gamma-aminobutyric acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.020

文献信息

• Asymmetric Synthesis of β-Substituted γ-Lactams Employing the SAMP-/RAMP-Hydrazone Methodology. Application to the Synthesis of (R)-(-)-Baclofen
  作者：Dieter Enders、Oliver Niemeier

  DOI：10.3987/com-05-s(k)41

  日期：——

  A short and efficient asymmetric synthesis of beta-substituted gamma-lactams is described. Key steps are the alpha-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The P-substituted gamma-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee = 93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (gamma-aminobutyric acids) is demonstrated for (R)-(-)-baclofen hydrochloride, which is obtained in 4 steps, 55% yield and 94% ee.
• [EN] METHOD FOR PREPARING CHIRAL GAMMA-LACTAM COMPOUND AND METAL COMPLEX THEREFOR<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ GAMMA-LACTAME CHIRAL ET COMPLEXE MÉTALLIQUE ASSOCIÉ<br/>[KO] 키랄 감마-락탐 화합물의 제조방법 및 이를 위한 금속 착체
  申请人：INST BASIC SCIENCE

  公开号：WO2020141734A1

  公开（公告）日：2020-07-09

  본 발명은 키랄 감마-락탐 화합물의 제조방법 및 이를 위한 신규 금속 착체에 관한 것으로, 본 발명의 키랄 감마-락탐 화합물의 제조방법은 키랄 에틸렌디아민 리간드를 포함하는 금속 착체를 촉매로 이용한 온화한 조건 하 프로키랄 1,4,2-디옥사졸-5-온 화합물로부터 우수한 거울상이성질선택성을 가진 키랄 감마-락탐 화합물을 효율적으로 제조할 수 있다.
• Intramolecular asymmetric C–H insertion of N-arylalkyl, N-bis(trimethylsilyl)methyldiazoamides mediated by chiral rhodium(II) catalysts. Synthesis of (R)-β-benzyl-γ-aminobutyric acid
  作者：Andrew G.H. Wee、Sammy C. Duncan、Gao-jun Fan

  DOI：10.1016/j.tetasy.2005.12.020

  日期：2006.1

  The enantio- and site-selectivity of the intramolecular C-H insertion reactions of acyclic N-arylalkyl, N-bis(trimethylsilyl)methyl alpha-diazoacetamides, and alpha-carboalkoxy-alpha-diazoacetamides 1a-g, catalyzed by chiral Rh(II) carboxamidates and Rh(II) carboxylates were studied. In general, the reaction showed good to excellent chemoselectivity. Regio selectivity for most of the reactions was high, but was also found to be influenced by the structure of the diazo substrate and the chiral Rh(II) catalyst employed. The highest enantioselectivity for the reactions catalyzed by chiral Rh(II) carboxamidates was 69% and Rh-2(4R-MEOX)(4) was found to be the most effective. For the chiral Rh(II) carboxylate catalyzed reactions, the highest ee obtained was 75% and Rh-2(S-PTTL)(4) is the optimal catalyst. The method was applied toward the synthesis of a GABA analogue, (R)-beta-benzyl-gamma-aminobutyric acid. (c) 2006 Elsevier Ltd. All rights reserved.