1-(naphthalene-2-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-one | 1152314-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(naphthalene-2-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-one
• 英文别名: 1-((naphthalen-2-yl)ethan-2-on-1-yl)-4-phenyl-1H-1,2,3-triazole；1-(naphthalene-6-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-ethanone；1-Naphthalen-2-yl-2-(4-phenyltriazol-1-yl)ethanone；1-naphthalen-2-yl-2-(4-phenyltriazol-1-yl)ethanone
• CAS: 1152314-69-6
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: VVTCFKTXIUFWRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(naphthalene-2-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-one 在 甲酸 、 [(R,R)-N-(2-amino-1,2-diphenylethyl)pentafluorobenzenesulfonamide]chloride(p-cymene)ruthenium (II) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以99%的产率得到(S)-1-(naphthalen-2-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-ol
  参考文献：
  名称：

  Catalytic asymmetric synthesis of β-triazolyl amino alcohols by asymmetric transfer hydrogenation of α-triazolyl amino alkanones

  摘要：

  The synthesis of optically active beta-triazolyl amino alcohols was carried out via ruthenium catalyzed asymmetric transfer hydrogenation of alpha-triazolyl amino alkanones. This reaction proceeds under mild reaction conditions with up to 99% yield and 99.9% enantiomeric excess (ee). This protocol was applied to the synthesis of an enantiopure antitubercular agent and its arylated product with retention in enantiomeric purity. The absolute configuration at the stereogenic center of the chiral product as found to be (S). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.012
• 作为产物：
  描述：

  苯乙炔 、 2-溴代-2-乙酰基萘 在 copper(l) iodide 、 sodium azide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以75%的产率得到1-(naphthalene-2-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethan-1-one
  参考文献：
  名称：

  InCl 3介导的生态友好型三组分多米诺反应，可在无溶剂条件下合成高度官能化的三唑基螺并恶臭多吡喃和三唑基吡喃†

  摘要：

  已经开发了一种一锅多米诺协议，用于有效合成新的三唑基螺并恶臭吲哚并吡喃和三唑基吡喃衍生物。合成是通过在InCl 3存在下，无溶剂条件下于100°C下使苯甲酰基三唑，靛红/芳香醛和活性亚甲基化合物反应来实现的。这种提供生物学上相关的杂环化合物的新策略大概涉及Knoevenagel缩合/ Michael加成/ 6-exo-dig-环化序列。

  DOI：

  10.1039/c4ra01524j

文献信息

• 18F-LABELED PRECURSOR OF PET RADIOACTIVE MEDICAL SUPPLIES, AND PREPARATION METHOD THEREOF
  申请人：Chi Dae-Yoon

  公开号：US20140194620A1

  公开（公告）日：2014-07-10

  The present invention relates to a precursor of positron emission tomography (PET) radioactive medical supplies, a preparation method thereof, and an application thereof, and more specifically, to a precursor having a tetravalent organic salt leaving group, a preparation method, and a method for preparing desired PET radioactive medical supplies in a high radiochemical yield within a short preparation time by introducing 18 F using the same through a single step. The precursor having a tetravalent organic salt leaving group of the present invention can simplify the known complex multistep preparation of radioactive medical supplies into a single step, can save production costs because an excessive amount of a phase transfer catalyst is not required, facilitates separation of a compound after reaction, and enables rapid reaction velocity. The features are appropriate for the mass production of PET radioactive medical supplies by an automated synthesis system.

  本发明涉及正电子发射断层扫描（PET）放射性医疗用品的前体、其制备方法及应用，更具体地，涉及一种具有四价有机盐离基的前体、其制备方法，以及通过引入 18 F并通过单步骤使用相同物质在短时间内高放射化学产率制备所需PET放射性医疗用品的方法。本发明的具有四价有机盐离基的前体可以将已知的复杂多步制备放射性医疗用品简化为单步骤，因为不需要过量的相转移催化剂，可以节省生产成本，促进反应后化合物的分离，并实现快速反应速度。这些特点适用于通过自动合成系统大规模生产PET放射性医疗用品。
• A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry
  作者：Dalip Kumar、V. Buchi Reddy、Rajender S. Varma

  DOI：10.1016/j.tetlet.2009.02.107

  日期：2009.5

  The reaction of α-tosyloxy ketones, sodium azide, and terminal alkynes in presence of copper(I) in aqueous polyethylene glycol afforded regioselectively 1,4-disubstituted 1,2,3-triazoles in good yield at ambient temperature. The one-pot exclusive formation of 1,4-disubstituted 1,2,3-triazoles involves in situ formation of α-azido ketones, followed by cycloaddition reaction with terminal alkyne. The

  α-甲苯磺酰氧基酮，叠氮化钠和末端炔在铜（I）存在下在聚乙二醇水溶液中反应在环境温度下以良好的产率提供区域选择性的1,4-二取代的1,2,3-三唑。一锅独家形成1,4-二取代1,2,3-三唑涉及原位形成α-叠氮基酮，然后与末端炔烃进行环加成反应。通过合成一系列不同的1,4-二取代的1,2,3-三唑，证明了这种一锅法的普遍性。
• An efficient Cu-catalyzed azide–alkyne cycloaddition (CuAAC) reaction in aqueous medium with a zwitterionic ligand, betaine
  作者：Jung-Ah Shin、Su-Jin Oh、Hee-Yoon Lee、Yeong-Gweon Lim

  DOI：10.1039/c7cy00518k

  日期：——

  Cu-catalyzed azide–alkyne cycloaddition reaction in aqueous medium was dramatically accelerated by a simple zwitterionic additive, betaine, at ambient temperature. In the presence of betaine, 1,4-disubstituted-1,2,3-triazoles were obtained from azides and terminal alkynes in excellent yields under 2.5–200 ppm levels of Cu(I) in water. This method resulted in the remarkable reduction of the Cu(I) concentration

  在环境温度下，简单的两性离子添加剂甜菜碱可显着促进水介质中铜催化的叠氮化物-炔烃环加成反应。在甜菜碱存在的情况下，在2.5–200 ppm的水中铜（I）水平下，叠氮化物和末端炔烃可得到1,4-二取代-1,2,3-三唑。该方法导致Cu （I）浓度显着降低至ppm级。该方案的优点包括使用常规的Cu催化体系和可商购获得的甜菜碱，该甜菜碱对生物应用通常是无毒的。因此，这种有效的催化体系应在生命科学研究和材料科学中具有广泛的应用。
• InCl3-mediated eco-friendly three-component domino reaction for synthesis of highly functionalized triazolylspiroxindolinopyrans and triazolylpyrans under solvent-free conditions
  作者：Jayabal Kamalraja、Potharaj Murugasan、Paramasivan Thirumalai Perumal

  DOI：10.1039/c4ra01524j

  日期：——

  A one pot domino protocol has been developed for the efficient synthesis of novel triazolylspiroxindolinopyrans and triazolylpyran derivatives. The synthesis was achieved by reacting phenacyltriazole, isatin/aromatic aldehyde and active methylene compounds in the presence of InCl3 under solvent-free conditions at 100 °C. This novel strategy affording biologically relevant heterocyclic compounds presumably

  已经开发了一种一锅多米诺协议，用于有效合成新的三唑基螺并恶臭吲哚并吡喃和三唑基吡喃衍生物。合成是通过在InCl 3存在下，无溶剂条件下于100°C下使苯甲酰基三唑，靛红/芳香醛和活性亚甲基化合物反应来实现的。这种提供生物学上相关的杂环化合物的新策略大概涉及Knoevenagel缩合/ Michael加成/ 6-exo-dig-环化序列。
• Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst
  作者：Jung-Ah Shin、Yeong-Gweon Lim、Kyung-Hee Lee

  DOI：10.1021/jo3000095

  日期：2012.4.20

  1,4-Disubstituted-1,2,3-triazoles were obtained in excellent yields from azides and terminal alkynes in H2O in the presence of catalytic amount of beta-cyclodextrin as a phase transfer catalyst. Also, a one-pot CuAAC reaction was carried out successfully, affording 1,4-disubstituted-1,2,3-triazoles in good to high yields starting from an alkyl bromide, sodium azide, and terminal alkyne.