1-(4-bromobenzyl)-4-(p-tolyl)-1H-1,2,3-triazole | 1352060-37-7

• 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-(4-bromobenzyl)-4-(p-tolyl)-1H-1,2,3-triazole
• 英文别名: 1-[(4-Bromophenyl)methyl]-4-(4-methylphenyl)triazole；1-[(4-bromophenyl)methyl]-4-(4-methylphenyl)triazole
• CAS: 1352060-37-7
• 化学式: C₁₆H₁₄BrN₃
• 分子量: 328.211
• InChiKey: KNQLLRNICROZTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-4-(p-tolyl)-1H-1,2,3-triazole 、 3-吡啶硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 3-(4-((4-(p-tolyl)-1H-1,2,3-triazol-1-yl)methyl)phenyl)pyridine
  参考文献：
  名称：

  Discovery of novel anti-angiogenesis agents. Part 10: Multi-target inhibitors of VEGFR-2, Tie-2 and EphB4 incorporated with 1,2,3-triazol

  摘要：

  VEGFR-2, Tie-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we developed a series of pyridines incorporated with 1,2,3-triazole as multi-target inhibitors based on the crystal structure alignment of the kinase domain of angiogenic RTKs. Biological results indicated that these multi-target inhibitors displayed considerable potential as novel anti-angiogenic agents. Among them, compound BD7 exhibited the most potent inhibition against the three RTKs simultaneously, and good activity on inhibiting viability of human umbilical endothelial cells. Therefore, 1,2,3-triazole could serve as a promising DFG binding group for multi-target inhibitors of VEGFR-2, Tie-2 and EphB4 bearing pyridine as hinge binding group. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.11.042
• 作为产物：
  描述：

  对溴溴苄 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 1-(4-bromobenzyl)-4-(p-tolyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Discovery of novel anti-angiogenesis agents. Part 9: Multiplex inhibitors suppressing compensatory activations of RTKs

  摘要：

  Aberrant angiogenesis is a hallmark of various diseases including cancers. VEGFR-2 inhibitors have been utilized as anti-angiogenic agents for several years. However, compensatory activation of various receptor tyrosine kinases (RTK) could induce the occurrence of resistance. We previously reported a series of multi-target inhibitors of VEGFR-2, Tie-2, and EphB4 as anti-angiogenic agents. These inhibitors might be a promising strategy to overcome the resistance induced by compensatory activation. In order to expand the structural diversity of these multiple RTK inhibitors, we described herein the design, synthesis, and evaluation of a novel class of triplet VEGFR-2/TIE-2/EphB4 inhibitors. The biological evaluation indicated that five compounds (6b, 6d, 6e, 7e, and 7g) exhibited simultaneous VEGFR-2/Tie-2/EphB4 inhibitory activities with IC50 values less than 50 nM. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.067

文献信息

• Large CuI8 chalcogenone cubic cages with non-interacting counter ions
  作者：Srinivas Katam、Prabusankar Ganesan

  DOI：10.1039/c7dt03796a

  日期：——

  anions, in which one of the PF6− anions occupies the centre of the Cu8 cube without any interaction. The copper(I) cubic cages are found to be highly active catalysts in click chemistry as well as hydroamination reactions. The scope of the catalytic reactions has been investigated with thirty-five different combinations of click reactions and six different combinations of the hydroamination of alkynes

  两个特大尺寸铜（我）立方笼，[的Cu（BPTP）1.5 } 8（PF 6 -）]（PF 6 - ）7（1）和[铜（黑花生衣色素）1.5 } 8（PF 6 -）] （PF 6 - ）7（2）中，由咪唑-2-硫属元素酮配体（支持BPTP = 2,6-双（1-异丙基-2-硫酮）吡啶和黑花生衣色素= 2,6-双（1-异丙基-2- -selone）pyridine）的合成和表征。离子盐的形成通过FT-IR，多核（1 H，13 C，31 P和19 F）NMR，UV-vis，TGA，CHN分析，BET分析，单晶X射线衍射和粉末X射线衍射确认1和2技术。据我们所知，这是在完美的立方结构中铜铜间距为8.413Å或8.593Å的八核铜（I）团簇的首例。有趣的是，这些以阴离子为中心的Cu I 8立方排列不受立方中心离子或面中心分子的支持。阳离子立方笼的形成伴随着十二种配体（Bptp或Bpsp）的结合。）具有八个三角形平面[CuSe
• Ultrasound promoted facile one pot synthesis of triazole derivatives catalyzed by functionalized graphene oxide Cu(I) complex under mild conditions
  作者：Hossein Naeimi、Rahele Shaabani

  DOI：10.1016/j.ultsonch.2016.05.043

  日期：2017.1

  A facile one pot three component reaction of alkyl halides, sodium azide with terminal alkynes can be catalyzed by functionalized graphene oxide copper (I) complex under ultrasonic irradiation at room temperature. In this protocol, the 1,4-disubstituted 1,2,3-triazoles were afforded as target pure products in excellent yields and short reaction times. The prepared catalyst has been characterized by

  在室温下超声辐射下，官能化的氧化石墨烯铜（I）配合物可催化烷基卤化物，叠氮化钠与末端炔烃的一锅三组分反应。在该方案中，以优异的产率和较短的反应时间提供了1,4-二取代的1,2,3-三唑作为目标纯产物。通过傅立叶变换红外光谱（FT-IR），X射线衍射光谱（XRD），能量分散X射线（EDX）和场发射扫描电子显微镜（FE-SEM）技术表征了所制备的催化剂。而且，该催化剂是化学选择性的和稳定的，并且可以重复使用几次，而其催化活性没有任何明显的损失。
• Nanocomposite copper metal as an efficient heterogeneous catalyst in click synthesis of 1,2,3-triazoles in aqueous media
  作者：Vajihe NEJADSHAFIEE、Hossein NAEIMI

  DOI：10.3906/kim-1610-57

  日期：——

  Copper/periodic mesoporous organosilica (Cu/PMO) nanocomposites provided a highly active, reusable, globular, solid-phase catalyst for click chemistry. The reaction proceeds by mixing organohalides, sodium azide, alkyne, and the catalyst in an aqueous medium to afford the desired products. The cost efficiency and recyclability of the catalyst up to six runs without appreciable loss of activity and

  铜/周期性介孔有机硅（Cu / PMO）纳米复合材料为点击化学提供了一种高活性，可重复使用的球状固相催化剂。通过在水性介质中混合有机卤化物，叠氮化钠，炔烃和催化剂进行反应，得到所需产物。催化剂的成本效益和可循环性（最多六次运行）没有明显的活性损失和高产物收率，使该过程更环保。
• β-CD/CuI catalyzed regioselective synthesis of iodo substituted 1,2,3-triazoles, imidazo[1,2-a]-pyridines and benzoimidazo[2,1-b]thiazoles in water and their functionalization
  作者：Divya Dheer、Ravindra K. Rawal、Virender Singh、P.L. Sangwan、Parthasarathi Das、Ravi Shankar

  DOI：10.1016/j.tet.2017.05.081

  日期：2017.7

  An environment benign process has been developed for the regioselective synthesis of 5-iodo-1,4-disubstituted-1,2,3-triazoles catalyzed by CuI/β-CD in water. Moreover, the process was manifested for the efficient synthesis of 2-iodo-imidazo[1,2-a]pyridines and 2-iodo-benzoimidazo[2,1-b]thiazoles in aqueous medium. Additionally, the iodinated derivatives were successfully modified via palladium catalyzed

  已经开发出一种环境友好的方法，用于在水中CuI /β-CD催化的5-碘-1,4-二取代-1,2,3-三唑的区域选择性合成。而且，在水性介质中有效合成2-碘-咪唑并[1,2- a ]吡啶和2-碘-苯并咪唑并[ 2,1- b ]噻唑的方法被证明。另外，通过钯催化的偶联反应成功地修饰了碘化衍生物。该方法的显着特征是在温和的反应条件下原位形成1-碘炔烃和烷基/芳基叠氮化物，高区域选择性以及使用水作为绿色溶剂。
• Cu(<scp>ii</scp>) PBS-bridged PMOs catalyzed one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles in water through click chemistry
  作者：Avvari N. Prasad、Benjaram M. Reddy、Eun-Young Jeong、Sang-Eon Park

  DOI：10.1039/c4ra04093g

  日期：——

  multicomponent reaction of benzyl halides with sodium azide and terminal alkynes. This catalyst allowed for the high regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles through a one-step and atom economic tandem reaction with water as the solvent. Note that no additional base or ligand or reducing agent is required. Moreover, in addition to benzyl halides, hetero benzyl halides have also been

  由1,2-双（三乙氧基甲硅烷基）乙烷和卟啉桥联倍半硅氧烷（PBS）的自组装合成了一系列的PBS- HPMO和Cu（II）-PBS-HPMO。这些合成的PBS- HPMO和Cu（II）-PBS-HPMO使用不同的光谱和非光谱技术进行了表征，即XRD，FT-IR光谱，氮吸附-解吸等温线以及UV可见光谱和EPR光谱。其中，卟啉桥联的PMO，特别是Cu（II）-PBS-HPMO被发现是苄基卤化物与叠氮化钠和末端炔烃多组分反应的有效催化剂。通过以水为溶剂的一步和原子经济级联反应，该催化剂可以实现1,4-二取代的1,2,3-三唑的高区域选择性合成。注意，不需要额外的碱或配体或还原剂。此外，除了苄基卤以外，杂苯苄基卤还以显着的产率和完全区域选择性的方式获得。通过采用该方案，还可以从易于获得的起始原料中制备出结构良好的1,2,3-三唑系列化合物，收率高至优异。此外，该过程纯粹是异质的，并且级联反应是在水中进行的，