(S)-N-(quinolin-3-yl)pyrrolidine-2-carboxamide | 478913-17-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-(quinolin-3-yl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-quinolin-3-ylpyrrolidine-2-carboxamide
• CAS: 478913-17-6
• 化学式: C₁₄H₁₅N₃O
• mdl: MFCD13212070
• 分子量: 241.293
• InChiKey: URINIHHQVZTZJF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl (2S)-2-(quinolin-3-ylcarbamoyl)pyrrolidine-1-carboxylate 在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以400 mg的产率得到(S)-N-(quinolin-3-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin

  摘要：

  We have screened a range of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts incorporating N-pyridyl and N-quinolinyl groups in the synthetically useful aldol reaction of isatin with acetone. The 'reverse amide' N-pyridyl pyrrolidinylmethyl amide catalysts proved highly catalytically active but gave disappointing enantioselectivities. However, an N-3-pyridyl prolinamide catalyst gave the aldol adduct in high yields and high enantioselectivity with up to 72% ee of the (S)-isomer. Conditions were optimised for this catalyst and in particular an additive screen identified a link between the pK(a) of the acid additive and the yield and enantioselectivity. An N-arylsulfonamide prolinamide was also identified as a catalyst for this reaction giving the (R)-enantiomer in 68% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.016

文献信息

• Dynamic assembly of a zinc-templated bifunctional organocatalyst in the presence of water for the asymmetric aldol reaction
  作者：Anna Serra-Pont、Ignacio Alfonso、Ciril Jimeno、Jordi Solà

  DOI：10.1039/c5cc07847d

  日期：——

  A bifunctional organocatalytic system consisting of simple pyridine ligands containing the separate catalytic functionalities was assembled using ZnCl2. This novel metal-templated catalyst furnished high yields and stereoselectivities towards the aldol...

  使用ZnCl2组装了一个双官能有机催化体系，该体系由简单的吡啶配体组成，该吡啶配体包含单独的催化官能团。这种新型的金属模板催化剂对醛醇缩合物提供了高收率和立体选择性。
• [EN] EFFLUX PUMP INHIBITORS<br/>[FR] INHIBITEURS DE POMPES D'ECOULEMENT
  申请人：MICROCIDE PHARMACEUTICALS INC

  公开号：WO2000001714A1

  公开（公告）日：2000-01-13

  Compounds are described which have efflux pump inhibitor activity. Also described are methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.
• Screening of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts for the enantioselective aldol reaction of acetone with isatin
  作者：Michael Kinsella、Patrick G. Duggan、Claire M. Lennon

  DOI：10.1016/j.tetasy.2011.07.016

  日期：2011.7

  We have screened a range of simple N-aryl and N-heteroaryl pyrrolidine amide organocatalysts incorporating N-pyridyl and N-quinolinyl groups in the synthetically useful aldol reaction of isatin with acetone. The 'reverse amide' N-pyridyl pyrrolidinylmethyl amide catalysts proved highly catalytically active but gave disappointing enantioselectivities. However, an N-3-pyridyl prolinamide catalyst gave the aldol adduct in high yields and high enantioselectivity with up to 72% ee of the (S)-isomer. Conditions were optimised for this catalyst and in particular an additive screen identified a link between the pK(a) of the acid additive and the yield and enantioselectivity. An N-arylsulfonamide prolinamide was also identified as a catalyst for this reaction giving the (R)-enantiomer in 68% ee. (C) 2011 Elsevier Ltd. All rights reserved.