1-苄基-4-(氯甲基)三唑 | 70380-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄基-4-(氯甲基)三唑
• 英文名称: 1-benzyl-4-(chloromethyl)-1H-1,2,3-triazole
• 英文别名: 1-benzyl-4-chloromethyl-1,2,3-triazole；1-benzyl-4-(chloromethyl)triazole
• CAS: 70380-29-9
• 化学式: C₁₀H₁₀ClN₃
• mdl: MFCD16748189
• 分子量: 207.662
• InChiKey: VDEJEUQPCJMKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-苄基-4-(氯甲基)三唑 在 sodium trithiocarbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 18.0h， 以62%的产率得到di-<(1-benzyl-1H-1,2,3-triazol-4-yl)-methylen>sulfide
  参考文献：
  名称：

  Biagi; Livi; Ramacciotti, Il Farmaco, 1990, vol. 45, # 1, p. 49 - 57

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苄基-4-(羟基甲基)-1H-1,2,3-噻唑 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到1-苄基-4-(氯甲基)三唑
  参考文献：
  名称：

  1,2,3-三唑姜黄素衍生物通过调节 MAPK/NF-κB/STAT3 信号通路的抗肺癌活性

  摘要：

  像1,2,3一样轻松呼吸：通过将1,2,3-三唑引入姜黄素的活性亚甲基，设计合成了一系列新型三唑姜黄素。生成的二氯取代苯基三唑甲基姜黄素在体外和体内均能有效抑制肿瘤细胞增殖并诱导肺癌细胞死亡，因此可能成为治疗非小细胞肺癌的潜在药物。

  DOI：

  10.1002/cmdc.202100676

文献信息

• Conventional and microwave assisted synthesis of 1,4-disubstituted 1,2,3-triazoles from Huisgen cycloaddition
  作者：Juan Ignacio Sarmiento-Sanchez、Adrian Ochoa-Teran、Ignacio A. Rivero

  DOI：10.3998/ark.5550190.0012.913

  日期：——

  In this paper the synthesis of a library of new 1,4-disubstituted 1,2,3-triazoles 1, with a variety of additional functional groups on its structure, from an in situ generated benzyl azide 2 and different alkynes and dialkynes 3 is reported. Optimal experimental conditions were established for the conventional click chemistry and for the microwave-assisted synthesis of these 1,2,3triazoles. Comparing

  在本文中，从原位生成的叠氮化苄 2 和不同的炔烃和二炔烃 3 合成了一个新的 1,4-二取代 1,2,3-三唑 1 库，其结构上具有多种附加官能团。报道。为常规点击化学和这些 1,2,3 三唑的微波辅助合成建立了最佳实验条件。比较结果可以得出结论，在微波辅助条件下，可以在更短的时间内以更高的产率获得产品。
• <i>Tris</i> ‐isocyanide copper(I) complex enabling copper azide‐alkyne cycloaddition in neat conditions
  作者：Valentina Ferraro、Roberto Sole、Marco Bortoluzzi、Valentina Beghetto、Jesús Castro

  DOI：10.1002/aoc.6401

  日期：2021.11

  determined by single-crystal X-ray diffraction. The complex is highly stable, active and selective toward the copper-catalyzed azide-alkyne cycloaddition, working in neat conditions and in the absence of bases at room temperature. Substrate scope was assessed by testing several different alkynes and azides. In most cases the corresponding 1,4-disubstituted-1,2,3-triazoles were isolated in high yields.

  在配位球中与 2,6-二甲基苯基异氰化物的三配位均配 Cu(I) 配合物很容易合成和分离为四氟硼酸盐。该化合物的结构由单晶X射线衍射确定。该配合物对铜催化的叠氮化物-炔烃环加成反应具有高度稳定性、活性和选择性，可在纯净条件下和室温下无碱条件下工作。通过测试几种不同的炔烃和叠氮化物来评估底物范围。在大多数情况下，相应的 1,4-二取代-1,2,3-三唑以高产率分离。
• Junjappa-Ila annulation: α-Oxoketene dithioacetal mediated synthesis of substituted benzotriazoles
  作者：Nitinkumar S. Shetty、Ravi S. Lamani、Shridhar I. Panchamukhi、Imtiyaz Ahmed M. Khazi

  DOI：10.1002/jhet.85

  日期：2009.7

  2-(1-Benzyl-1H–1,2,3-triazole-4-yl)-3-methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile with various α-oxoketene dithioacetals in the presence of sodium hydride. The intermediates underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles in moderate yields. J. Heterocyclic

  2-（1-苄基-1 H –1,2,3-三唑-4-基）-3-甲基硫烷基-5-氧代-5-取代的戊-2-烯腈通过以良好产率得到缩合的（1-苄基-1 H -1,2,3-三唑-4-基）乙腈 与各种α-氧杂环丁烯二硫缩醛 在氢化钠存在下。中间体在PTSA的存在下进行酸诱导的环化反应，得到相应的苯并三唑产量中等。J.杂环化​​学，（2009）。
• α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 1. (Imidazolylmethyl)oxazoles and -thiazoles
  作者：Robert E. Boyd、Jeffery B. Press、C. Royce Rasmussen、Robert B. Raffa、Ellen E. Codd、Charlene D. Connelly、Debra J. Bennett、Alex L. Kirifides、Joseph F. Gardocki、Brian Reynolds、John T. Hortenstein、Allen B. Reitz

  DOI：10.1021/jm990005a

  日期：1999.12.1

  A series of (imidazolylmethyl)oxazoles and -thiazoles were prepared and evaluated as alpha(2) adrenoceptor agonists. These compounds were also tested in in vivo paradigms that are predictive of analgesic activity. Variations in both the imidazole and thiazole portions of the molecule were investigated. Some of the more potent compounds such as 22, 26, 45, and 53 displayed at receptor binding in the 10-20 nM range and also had significant, antinociceptive activity in the mouse abdominal irritant test (MAIT).
• An Abnormal N-Heterocyclic Carbene-Copper(I) Complex in Click Chemistry
  作者：Samaresh Chandra Sau、Sudipta Raha Roy、Tamal K. Sen、Dinesh Mullangi、Swadhin K. Mandal

  DOI：10.1002/adsc.201300343

  日期：2013.10.11

  AbstractHerein we report the synthesis of a copper(I) chloro complex using an abnormal N‐heterocyclic carbene (aNHC) salt, 1,3‐bis(2,6‐diisopropylphenyl)‐2,4‐diphenylimidazolium. The CuCl(aNHC) complex efficiently catalyzed Huisgen 1,3‐dipolar cycloaddition reactions (click reactions) of azides with alkynes to give 1,4‐substituted 1,2,3‐triazoles in excellent yields at room temperature within short reaction time under solvent‐free conditions. The catalyst successfully activated benzyl azide and phenylacetylene under the low catalyst loading of 0.005 mol% resulting in a nearly quantitative yield of the product at room temperature with the high TON value of 19,800. The catalyst also exhibits high efficiency in the reaction between sterically hindered azides and alkynes under solvent‐free conditions at room temperature. Furthermore, a number of internal alkynes was successfully tested in this copper‐catalyzed cycloaddition reaction for synthesis of 4,5‐disubstituted triazoles.magnified image