(2S)-2-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine | 918313-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2S)-2-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine
• 英文别名: 4-phenyl-1-(((S)-pyrrolidin-2-yl)methyl)-1H-1,2,3-triazole；4-phenyl-1-{[(S)-pyrrolidin-2-yl]methyl}-1H-1,2,3-triazole；(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole；(S)-(2-(4-phenyltriazolyl)methyl)pyrrolidine；1H-1,2,3-Triazole, 4-phenyl-1-[(2S)-2-pyrrolidinylmethyl]-；4-phenyl-1-[[(2S)-pyrrolidin-2-yl]methyl]triazole
• CAS: 918313-38-9
• 化学式: C₁₃H₁₆N₄
• 分子量: 228.297
• InChiKey: NJRFUIBZODLJFT-LBPRGKRZSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  416.4±37.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine 、 环丙基萘啶羧酸 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  The synthesis and biological evaluation of a novel series of C7 non-basic substituted fluoroquinolones as antibacterial agents

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.06.006
• 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 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 19.5h， 生成 (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
• 作为试剂：
  描述：

  5-((E)-2-nitroethenyl)-1,3-benzodioxole 、 环己酮 在 (2S)-2-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine 作用下， 以 水 为溶剂， 反应 20.0h， 生成 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)cyclohexanone 、 (S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone
  参考文献：
  名称：

  Combining proline and ‘click chemistry’: a class of versatile organocatalysts for the highly diastereo- and enantioselective Michael addition in water

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.12.003

文献信息

• Hollow structural effect of microporous organocatalytic polymers with pyrrolidines: dramatic enhancement of catalytic performance
  作者：Kyoungil Cho、Jin Yoo、Hyeong-Wan Noh、Sang Moon Lee、Hae Jin Kim、Yoon-Joo Ko、Hye-Young Jang、Seung Uk Son

  DOI：10.1039/c7ta02404e

  日期：——

  Hollow and microporous organocatalytic polymers bearing pyrrolidines (H-MOP-P) were prepared by template synthesis and post-synthetic modification and showed enhanced performance, compared to nonhollow ones.

  空心和微孔有机催化聚合物（H-MOP-P）通过模板合成和后合成修饰制备，与非空心聚合物相比表现出更好的性能。
• 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
• Influence of steric demand on ruthenium-catalyzed cycloaddition of sterically hindered azides
  作者：Venkata S. Sadu、Sirisha Sadu、Seji Kim、In-Taek Hwang、Ki-Jeong Kong、Kee-In Lee

  DOI：10.1039/c6ra25403a

  日期：——

  The RuAAC of sterically hindered 2,2-diaryl-2-azidoamines and terminal alkynes resulted in the unprecedented formation of 1,4-disubstituted-1,2,3-triazoles. A control experiment with 2-(azidomethyl)pyrrolidine revealed the usual selectivity with RuAAC and the reactions of azides with intermediate bulkiness gave mixtures of 1,4- and 1,5-regioisomers. The results suggest that the steric demands could

  空间受阻的2,2-二芳基-2-叠氮基胺和末端炔烃的RuAAC导致空前形成1,4-二取代-1,2,3-三唑。用2-（叠氮甲基）吡咯烷的对照实验表明，通常用RuAAC具有选择性，叠氮化物在中等体积下的反应得到1，4-和1，5-区域异构体的混合物。结果表明，空间需求可以基本消除RuAAC的偏好和对区域选择性的影响。
• SiO2–NHC–Cu(I): an efficient and reusable catalyst for [3+2] cycloaddition of organic azides and terminal alkynes under solvent-free reaction conditions at room temperature
  作者：Pinhua Li、Lei Wang、Yicheng Zhang

  DOI：10.1016/j.tet.2008.09.021

  日期：2008.11

  highly efficient catalyst for [3+2] cycloaddition of organic azides and terminal alkynes. In the presence of SiO2–NHC–Cu(I) 3b (1 mol %), the reactions of terminal alkynes with organic azides underwent smoothly to generate the corresponding regiospecific 1,4-disubstituted 1,2,3-triazoles in excellent yields under solvent-free reaction conditions at room temperature. Furthermore, catalyst 3b was quantitatively

  一种新型的SiO 2 -NHC-Cu（I）3b被开发出来并用作有机叠氮化物和末端炔烃的[3 + 2]环加成反应的高效催化剂。在SiO 2 -NHC-Cu（I）3b（1 mol％）的存在下，末端炔烃与有机叠氮化物的反应顺利进行，从而以优异的收率生成了相应的区域特异性的1,4-二取代的1,2,3-三唑在室温下在无溶剂的反应条件下进行。此外，通过简单的过滤从反应混合物中定量地回收了催化剂3b，并在不损失其活性的情况下重复使用了10个循环。
• PREPARATION METHOD OF CHIRAL MULTIPLE SUBSTITUTED TETRAHYDROPYRAN
  申请人：National Taiwan Normal University

  公开号：US20160355495A1

  公开（公告）日：2016-12-08

  An organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols via Michael/acetalization sequence to give fully substituted tetrahydropyranols is described. The process affords the products with high to excellent stereoselectivities. The highly enantioenriched, less reactive (S)-nitroallylic alcohols were isolated with good to high chemical yields. The synthetic application of the resolved substrate is shown toward the synthesis of enantioenriched (+)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid.

  本文介绍了一种通过Michael/缩醛化序列的有机催化动力学拆分手性二级硝基烯丙醇，制备全取代的四氢吡喃醇的方法。该过程具有高到极好的立体选择性。高对映选择性、反应性较差的(S)-硝基烯丙醇以良好到高的化学收率分离出来。本文还展示了解决的底物在合成对映富集的(+)-(2S,3R)-3-氨基-2-羟基-4-苯基丁酸方面的应用。