(1-hexyl-1H-1,2,3-triazol-4-yl)methanol | 1041262-17-2

• 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-hexyl-1H-1,2,3-triazol-4-yl)methanol
• 英文别名: (1-hexyltriazol-4-yl)methanol
• CAS: 1041262-17-2
• 化学式: C₉H₁₇N₃O
• 分子量: 183.253
• InChiKey: QSKIRFHROMPAJE-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  327.9±34.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-hexyl-1H-1,2,3-triazol-4-yl)methanol 在 AMBERLITE IRA₄₀₀OH 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 40.0h， 生成 (1-Hexyl-3-propyltriazol-1-ium-4-yl)methanol;acetate
  参考文献：
  名称：

  Effect of 1,2,3-triazole salts, non-classical bioisosteres of miltefosine, on Leishmania amazonensis

  摘要：

  Here, we report the effect of new non-classical bioisosteres of miltefosine on Leishmania amazonensis. Fifteen compounds were synthesized and the compound dhmtAc, containing an acetate anion, a side chain of 10 carbon atoms linked to N-1 and a methyl group linked to N-3, showed high and selective biological activity against L. amazonensis. On the intracellular amastigotes, stages of the parasite related to human disease, the IC50 values were near or similar to the 1.0 mu M (0.9, 0.8 and 1.0 mu M on L. amazonensis-WT, and two transgenic L. amazonensis expressing GFP and RFP, respectively), being more active than miltefosine. Furthermore, dhmtAc did not show toxic effects on human erythrocytes and macrophages (CC50 = 115.91 mu M) being more destructive to the intracellular parasites (selectivity index > 115). Promastigotes and intramacrophage amastigotes treated with dhmtAc showed low capacity for reversion of the effect of the compound. A study of the mechanism of action of this compound showed some features of metazoan apoptosis, including cell volume decreases, loss of mitochondrial membrane potential, ROS production, an increase in the intracellular lipid bodies, in situ labeling of DNA fragments by TUNEL labeling and phosphatidylserine exposure to the outerleaflet of the plasma membrane. In addition, the plasma membrane disruption, revealed by PI labeling, suggests cell death by necrosis. No increase in autophagic vacuoles formation in treated promastigotes was observed. Taken together, the data indicate that the bioisostere of miltefosine, dhmtAc, has promising antileishmanial activity that is mediated via apoptosis and necrosis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.051
• 作为产物：
  描述：

  溴己烷 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (1-hexyl-1H-1,2,3-triazol-4-yl)methanol
  参考文献：
  名称：

  Effect of 1,2,3-triazole salts, non-classical bioisosteres of miltefosine, on Leishmania amazonensis

  摘要：

  Here, we report the effect of new non-classical bioisosteres of miltefosine on Leishmania amazonensis. Fifteen compounds were synthesized and the compound dhmtAc, containing an acetate anion, a side chain of 10 carbon atoms linked to N-1 and a methyl group linked to N-3, showed high and selective biological activity against L. amazonensis. On the intracellular amastigotes, stages of the parasite related to human disease, the IC50 values were near or similar to the 1.0 mu M (0.9, 0.8 and 1.0 mu M on L. amazonensis-WT, and two transgenic L. amazonensis expressing GFP and RFP, respectively), being more active than miltefosine. Furthermore, dhmtAc did not show toxic effects on human erythrocytes and macrophages (CC50 = 115.91 mu M) being more destructive to the intracellular parasites (selectivity index > 115). Promastigotes and intramacrophage amastigotes treated with dhmtAc showed low capacity for reversion of the effect of the compound. A study of the mechanism of action of this compound showed some features of metazoan apoptosis, including cell volume decreases, loss of mitochondrial membrane potential, ROS production, an increase in the intracellular lipid bodies, in situ labeling of DNA fragments by TUNEL labeling and phosphatidylserine exposure to the outerleaflet of the plasma membrane. In addition, the plasma membrane disruption, revealed by PI labeling, suggests cell death by necrosis. No increase in autophagic vacuoles formation in treated promastigotes was observed. Taken together, the data indicate that the bioisostere of miltefosine, dhmtAc, has promising antileishmanial activity that is mediated via apoptosis and necrosis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.051

文献信息

• NNN-pincer-copper complex immobilized on magnetic nanoparticles as a powerful hybrid catalyst for aerobic oxidative coupling and cycloaddition reactions in water
  作者：Nasrin Zohreh、Mahboobeh Jahani

  DOI：10.1016/j.molcata.2016.11.007

  日期：2017.1

  such as SEM, TEM, FT-IR, TGA, ICP, XRD, and elemental analysis. The finely engineered supported catalyst is employed in the aerobic oxidative coupling of terminal alkynes and click reaction using only 0.38 and 0.04 mol% catalyst, respectively. All reactions perform under solvent-free condition or green solvent H 2 O. Also, the catalyst is readily recovered and reused for up to 8 and 6 subsequent runs

  摘要 描述了一种简单可靠的方法，用于制备第一个对表面组成具有高度控制的非均相 NNN-钳形铜杂化催化剂。该策略依赖于 2-氨基吡啶与三聚氯氰功能化磁性纳米粒子的共价键合，然后与 CuI 络合。这些声明通过不同的表征方法得到证实，例如 SEM、TEM、FT-IR、TGA、ICP、XRD 和元素分析。精细设计的负载型催化剂用于末端炔烃的有氧氧化偶联和点击反应，分别仅使用 0.38 和 0.04 mol% 的催化剂。所有反应均在无溶剂条件或绿色溶剂 H 2 O 下进行。此外，
• Synthesis of novel 1,4-disubstituted 1,2,3-triazoles bearing organosilicon-sulfur groups via the click reaction sonocatalyzed by LaCu_xMn_1-xO₃ nanoparticles
  作者：Kazem D. Safa、Hanieh Mousazadeh

  DOI：10.1080/00397911.2016.1217339

  日期：2016.10.1

  ABSTRACT A highly efficient and environmentally friendly one-pot procedure for the synthesis of 1,2,3-triazoles by 1,3-dipolar cycloaddition of benzyl halides, terminal alkynes, and sodium azide over LaCuxMn1-xO3 perovskite oxides was developed. LaCu0.7Mn0.3O3 was found to be active with low catalyst loading under ultrasonic irradiation in aqueous media. The reaction was performed efficiently in the presence

  摘要 开发了一种高效、环保的一锅法，用于在 LaCuxMn1-xO3 钙钛矿氧化物上通过苄基卤化物、末端炔烃和叠氮化钠的 1,3-偶极环加成反应合成 1,2,3-三唑。发现 LaCu0.7Mn0.3O3 在水介质中超声辐照下具有低催化剂负载量的活性。在没有任何添加剂或碱的情况下，在纳米催化剂的存在下，反应有效地进行，反应时间显着减少。催化剂可以循环使用至少5次，对反应结果没有任何显着影响。此外，使用二硫化碳和三（三甲基甲硅烷基）甲基锂合成了一系列新型有机硅硫取代的 1,2,3-三唑衍生物。图形概要
• Regioselective synthesis of 1,4-disubstituted triazoles using bis[(L)prolinato-N,O]Zn complex as an efficient catalyst in water as a sole solvent
  作者：Mazaahir Kidwai、Arti Jain

  DOI：10.1002/aoc.1816

  日期：2011.8

  A concise, convenient and mild route for one‐pot regioselective synthesis of N‐aryl‐ and N‐alkyltriazoles in water as a sole solvent is reported. The methodology involves a three‐component reaction comprising aryl/alkyl‐alkyne, sodium azide and aryl/alkyl/allyl halide catalyzed by zinc(II) L‐prolinate. Prominent features of our protocol are incorporation of transition metal catalyst other than copper

  据报导，在水中作为唯一溶剂的N-芳基和N-烷基三唑的单锅区域选择性合成的简洁，便捷和温和的路线。本方法涉及的三组分反应，其包括芳基/烷基炔烃，叠氮化钠和芳基/烷基/烯丙基卤催化由锌（II）大号-prolinate。我们协议的突出特点是掺入了除铜以外的过渡金属催化剂，水作为反应介质，催化剂的可回收性以及避免了危险的芳基叠氮化物作为反应物。版权所有©2011 John Wiley＆Sons，Ltd.
• A bile acid-based pyridino-triazole ligand for Cu(I)-stabilization and its application in Cu(I) catalyzed click reactions
  作者：Aradhana Nayal、Pramod S. Pandey

  DOI：10.1016/j.tetlet.2020.152509

  日期：2020.11

  A bile acid based pyridino-triazole ligand to stabilize Cu(I) state has been developed. The ligand was found to catalyze click reactions of a number of alkynes and azides in presence of Cu(CH3CN)4.BF4 at very low catalyst loading and under milder reaction conditions.

  已经开发了基于胆汁酸的吡啶三唑配体来稳定Cu（I）状态。发现该配体在非常低的催化剂负载量和较温和的反应条件下在Cu（CH 3 CN）4 .BF 4存在下催化许多炔烃和叠氮化物的点击反应。
• A One-Pot Synthesis of Constitutionally Unsymmetrical Rotaxanes Using Sequential CuI-Catalyzed Azide–Alkyne Cycloadditions
  作者：Jason M. Spruell、William R. Dichtel、James R. Heath、J. Fraser Stoddart

  DOI：10.1002/chem.200800067

  日期：2008.5.9

  A one-pot sequential Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection

  提出了一锅顺序Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）策略，用于从简单的起始原料以高收率合成结构不对称的基于环双（百草枯-对苯撑）的轮烷。该方法包括逐步进行多个CuAAC反应以终止假轮烷，其顺序通过末端炔基的甲硅烷基保护和Ag（I）催化的脱保护作用来控制。两亲性支链[4]轮烷的合成突出了该方法。该方法提高了访问越来越复杂的机械互锁化合物以在设备中用作复杂和功能性分子机械的能力。