(S)-tert-butyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyrrolidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-tert-butyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[(4-phenyltriazol-1-yl)methyl]pyrrolidine-1-carboxylate
• 化学式: C₁₈H₂₄N₄O₂
• 分子量: 328.414
• InChiKey: AKPNAJGEYHEPRY-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到(2S)-2-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine
  参考文献：
  名称：

  脯氨酸衍生的氨基三唑配体：在钌催化的不对称转移加氢中的制备和使用

  摘要：

  2-三唑基和由2- triazolylmethylpyrrolidines的制备大号脯氨酸和大号-反式-4-羟基脯氨酸进行了说明，以它们作为钌催化不对称转移氢化手性配体的评价沿。还介绍了通过引入远程取代基进行配体的模块化演化，显示出对配体性能的出乎意料的重要影响。

  DOI：

  10.1002/adsc.201000678
• 作为产物：
  描述：

  (S)-2-(甲苯磺酰氧基甲基)吡咯烷-1-甲酸叔丁酯 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 水 、 sodium ascorbate 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 19.0h， 生成 (S)-tert-butyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  脯氨酸衍生的氨基三唑配体：在钌催化的不对称转移加氢中的制备和使用

  摘要：

  2-三唑基和由2- triazolylmethylpyrrolidines的制备大号脯氨酸和大号-反式-4-羟基脯氨酸进行了说明，以它们作为钌催化不对称转移氢化手性配体的评价沿。还介绍了通过引入远程取代基进行配体的模块化演化，显示出对配体性能的出乎意料的重要影响。

  DOI：

  10.1002/adsc.201000678

文献信息

• Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts
  作者：Feng An、Biplab Maji、Elizabeth Min、Armin R. Ofial、Herbert Mayr

  DOI：10.1021/jacs.9b11877

  日期：2020.1.22

  the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale

  有机催化反应中常用的 32 种吡咯烷和咪唑烷酮的 Brønsted 碱度 pKaH（即共轭酸的 pKa）已在乙腈溶液中使用 CH 酸作为指示剂通过光度法测定。大多数研究的吡咯烷的碱性范围为 16 < pKaH < 20，而咪唑烷酮的碱性明显较低 (10 < pKaH < 12)。2-(三氟甲基)吡咯烷 (A14, pKaH 12.6) 和 2-咪唑鎓甲基取代的吡咯烷 A21 (pKaH 11.1) 超出了吡咯烷的典型范围，其碱度与咪唑烷酮的碱度相当。这 32 种有机催化剂与二苯甲基离子 (Ar2CH+) 和结构相关的醌甲基化物（用于量化亲核反应性的常见参考亲电试剂）的反应动力学已通过光度计测量。大多数反应遵循二级动力学，胺一级反应，亲电试剂一级反应。由于胺在亲电子试剂上的初始攻击的可逆性，随后中间体铵离子的速率决定性去质子化，观察到咪唑烷酮和几种携带大量 2-取代基的吡咯烷的反应更复杂的动力学。在
• (<i>S</i>)-Pyrrolidin-2-ylmethyl-1,2,3-triazolium Salts - Ionic Liquid Supported Organocatalysts for Enantioselective Michael Additions to β-Nitrostyrenes
  作者：Jürgen Liebscher、Zekarias Yacob、Jabbar Shah、Joachim Leistner

  DOI：10.1055/s-2008-1078593

  日期：——

  (S)-Pyrrolidin-2-ylmethyl-1,2,3-triazolium salts were synthesized as new task-specific ionic liquids via click reaction and alkylation. They serve as excellent recyclable catalysts in enantioselective Michael additions to nitrostyrenes in excess of carbonyl compounds as reactant and as solvent providing high yields and stereoselectivities.

  (S)-Pyrrolidin-2-ylmethyl-1,2,3-triazolium 盐通过点击反应和烷基化合成为新的任务特定离子液体。它们在作为反应物和溶剂提供高产率和立体选择性的硝基苯乙烯对映选择性迈克尔加成反应中用作优异的可回收催化剂，作为反应物和溶剂。
• Palladium complexes with abnormal N-heterocyclic carbene ligands derived from 1,2,3-triazolium ions and their application in Suzuki coupling
  作者：Thandavamurthy Karthikeyan、Sethuraman Sankararaman

  DOI：10.1016/j.tetlet.2009.08.002

  日期：2009.10

  Chiral and achiral pincer type palladium complexes bearing abnormal N-heterocyclic carbene ligands derived from 1,2,3-triazole are reported. Both complexes are effective as catalysts for non-asymmetric Suzuki coupling reaction for the synthesis of biphenyl derivatives. However, both the complexes failed to catalyze the formation of binaphthyl derivatives, by the asymmetric Suzuki coupling in case of

  报道了带有异常的衍生自1,2,3-三唑的N-杂环卡宾配体的手性和非手性钳型钯配合物。两种配合物都可有效地用作非对称Suzuki偶联反应的催化剂，用于合成联苯衍生物。然而，通过手性络合物的不对称Suzuki偶联和在非手性钳形络合物的情况下的非不对称形式，两种络合物均不能催化联萘衍生物的形成。相反，芳基硼酸的脱硼非常有效地发生，而芳基溴化物保持完整。
• The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents
  作者：Xiaoguang Huang、Dongliang Chen、Ning Wu、Aiqin Zhang、Zhenhua Jia、Xingshu Li

  DOI：10.1016/j.bmcl.2009.06.006

  日期：2009.8

  A series of non-basic building blocks was synthesized and introduced to the C7 position of the quinolone nucleus 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid to afford the corresponding. fluoroquinolones in 46-85% yield. The antibacterial activity of these new. fluoroquinolones was evaluated using a standard broth microdilution technique. The sulfur-containing quinolone, 7-(2-thia-5-azabicyclo[2.2.1]heptan-5-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid exhibited a superior antibacterial activity against quinolone-susceptible and multidrug-resistant strains in comparison with the clinically used fluoroquinolones ciprofloxacin and vancomycin, especially to the Streptococcus pneumonia and multidrug-resistant S. pneumonia clinical isolates. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• Combining proline and ‘click chemistry’: a class of versatile organocatalysts for the highly diastereo- and enantioselective Michael addition in water
  作者：Ze-Yi Yan、Yan-Ning Niu、Hai-Long Wei、Lu-Yong Wu、Ya-Bin Zhao、Yong-Min Liang

  DOI：10.1016/j.tetasy.2006.12.003

  日期：2006.12

  Based on 'click chemistry' conditions, a class of novel, facile, versatile pyrrolidine-based triazole derivatives were prepared, and proved to be efficient catalysts for the highly diastereoselective and enantioselective Michael addition of ketones to nitroalkenes. The Cu(I)-catalyzed 1,3-dipolar 'click' azide-alkyne cycloaddition provides modular and tunable features for the pyrrolidine-based triazole organocatalysts, and the resulting triazole moiety can serve as a phase tag to complete the reaction in water with an excellent yield and high enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.