1-benzyl-5-butyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-5-butyl-1H-1,2,3-triazole
• 英文别名: 1-benzyl-5-butyltriazole
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: TXPNOVWRHJSOTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄胺 在 N-甲基咪唑 、 亚硝酸特丁酯 、 叠氮基三甲基硅烷 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 、 乙腈 为溶剂， 反应 74.0h， 生成 1-benzyl-5-butyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Zinc Mediated Azide–Alkyne Ligation to 1,5- and 1,4,5-Substituted 1,2,3-Triazoles

  摘要：

  A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.

  DOI：

  10.1021/ol402225d

文献信息

• A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
  作者：Guolin Cheng、Xiaobao Zeng、Jinhai Shen、Xuesong Wang、Xiuling Cui

  DOI：10.1002/anie.201307499

  日期：2013.12.9

  About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α‐amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see

  关于细节：已经建立了通过空前的迈克尔加成/去酰基重氮转移/环化序列进行区域特异性合成标题化合物的方法。简单实用的方法可用于伯胺（包括手性α-胺）的修饰。该过程涉及三个共价键的形成和两个共价键的裂解（参见方案，Ts = 4-甲苯磺酰基）。
• Preparation, Characterization, and Reactivity of Azido Complex Containing a Tp(^<i>t</i>BuNC)(PPh₃)Ru Fragment and Ruthenium-Catalyzed Cycloaddition of Organic Azides with Alkynes in Organic and Aqueous Media
  作者：Yih-Hsing Lo、Tsang-Hsiu Wang、Chia-Yi Lee、Ying-Hsuan Feng

  DOI：10.1021/om300687a

  日期：2012.10.8

  five-membered cyclic oxycarbene complex (PPh3)[Ru]═C4H6O}+ (11). Several cationic imine complexes (tBuNC)[Ru]-(NH═CHR′)}+ (12a, R′ = H; 12b, R′ = CH3; 12c, R′ = Ph) are formed by the reaction of RCH2X with 2. If the reaction of 2 with CH3I is carried out at 35 °C for 24 h, (tBuNC)[Ru]-I (13) could be isolated. Preliminary results on the catalytic activity of 2 are also presented. Complex 2 catalyzes cycloaddition

  用过量的叠氮化钠处理TpRu络合物（PPh 3）[Ru] -Cl（1，[Ru] = Tp（t BuNC）Ru）得到黄色钌叠氮基络合物（PPh 3）[Ru] -N 3（2）。所述三唑合复合物（PPH 3）的[Ru] -N 3 Ç 2（R）2（图3a，R =甲基;图3b，R = ET）经由合成[3 + 2]环加成的2用RO 2 CC≡CCO 2 R.这些triazolato配合物的完整表征阐明了结构，并确定了加成产物的N（2）键类型。的烷基化3a与有机溴化物引起Ru–N键断裂，并提供1,4,5-三取代的三唑。此外，除了CS的2至2产生热不稳定thiothiatriazolate（PPH 3）的[Ru] -N 3 CS（S）（5），其转换成异硫氰酸酯复合物（PPH 3）的[Ru] -NCS（6）和（t BuNC）[Ru] -NCS（7）。其他试剂也可与2反应，但产物不是由[3 + 2]环加成反应产生的。在H
• Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation
  作者：Lindsay E. Chatkewitz、John F. Halonski、Marshall S. Padilla、Douglas D. Young

  DOI：10.1016/j.bmcl.2017.12.007

  日期：2018.1

  The prevalence of 1,3-dipolar cycloadditions of azides and alkynes within both biology and chemistry highlights the utility of these reactions. However, the use of a copper catalyst can be prohibitive to some applications. Consequently, we have optimized a copper-free microwave-assisted reaction to alleviate the necessity for the copper catalyst. A small array of triazoles was prepared to examine the

  在生物学和化学领域中，叠氮化物和炔烃的1,3-偶极环加成反应的普遍性突出了这些反应的效用。但是，铜催化剂的使用对于某些应用可能是禁止的。因此，我们优化了无铜微波辅助反应，以减轻铜催化剂的必要性。制备了一小批三唑来检验这种方法的范围，并将该方法通过使用非天然氨基酸转化为蛋白质，以证明涉及全长蛋白质的首批微波介导的生物缀合物之一。
• Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: new mechanistic features
  作者：Longcheng Hong、Weijia Lin、Fangjun Zhang、Ruiting Liu、Xigeng Zhou

  DOI：10.1039/c3cc42534g

  日期：——

  The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mechanistic features involving a tandem anionic cascade cyclization and anti-addition across the CC triple bond.

  首例稀土金属催化的末端炔烃与叠氮化合物的环加成反应，生成1,5-二取代的1,2,3-三唑，已被报道。初步研究表明，这一环加成反应展现出前所未有的机理特征，涉及串联的阴离子级联环化和反式加成穿过碳碳三键。
• A recyclable ruthenium(ii) complex supported on magnetic nanoparticles: a regioselective catalyst for alkyne–azide cycloaddition
  作者：Dong Wang、Lionel Salmon、Jaime Ruiz、Didier Astruc

  DOI：10.1039/c3cc43048k

  日期：——

  A magnetically separable ruthenium catalyst was synthesized through immobilizing a pentamethylcyclopentadienyl ruthenium complex on iron oxide nanoparticles. The catalyst is highly active and selective for the synthesis of 1,5-disubstituted 1,2,3-trizoles via cycloaddition of alkynes and organic azides and can be recycled at least 5 times.

  通过将五甲基环戊二烯基钌络合物固定在氧化铁纳米颗粒上来合成可磁分离的钌催化剂。该催化剂对炔烃和有机叠氮化物的环加成反应具有很高的活性，对合成1,5-二取代的1,2,3-三唑具有选择性，可循环使用至少5次。