4-(2-methoxynaphthalen-1-yl)-2H-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-methoxynaphthalen-1-yl)-2H-triazole
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: DLHVRGNHUCIEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-环己烯-1-酮 、 4-(2-methoxynaphthalen-1-yl)-2H-triazole 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以66%的产率得到3-(4-(2-methoxynaphthalen-1-yl)-2H-1,2,3-triazol-2-yl)cyclohexanone
  参考文献：
  名称：

  DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles

  摘要：

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.11.125
• 作为产物：
  描述：

  2-Methoxy-1-(2-nitroethenyl)naphthalene 在 sodium azide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-methoxynaphthalen-1-yl)-2H-triazole
  参考文献：
  名称：

  DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles

  摘要：

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.11.125

文献信息

• Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles by N2-Selective Aza-Michael Addition
  作者：Ujjawal Kumar Bhagat、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.7b02793

  日期：2018.1.19

  of this reaction have only recently been developed. Nevertheless, functionalization at the N2-position of NH-1,2,3-triazoles leading to optically active N2-substituted triazoles is not yet developed. In this article, we report, for the first time, the asymmetric aza-Michael reaction of 4-aryl-NH-1,2,3-triazoles to cyclic enones under the catalytic influence of chiral bifunctional thiourea organocatalysts

  尽管N个N1-官能^ h -1,2,3-三唑已经知道了几十年，这种反应的对映选择性变种最近才开发的。然而，尚未开发出在N H -1,2,3-三唑的N2-位上的官能化导致光学活性的N2-取代的三唑。在本文中，我们首次报道了在手性双官能硫脲有机催化剂的催化作用下，4-芳基-N H -1,2,3-三唑与环烯酮的不对称氮杂-迈克尔反应，生成对映体。 2,4-二取代的1,2,3-三唑。辛可宁衍生的硫脲催化剂III 在当前的转换中有效地工作，以生产N2官能化的1,2,3-三唑为主要产品，光学收率高达> 99.9％，以及次要的1,4-二取代的1,2,3-三唑。
• Base-Mediated Ring Opening of meso-Epoxides with 4-Aryl-NH-1,2,3-triazoles: Synthesis of trans-2-(Aryltriazolyl)cycloalkanols
  作者：Ujjawal Bhagat、Rama Peddinti

  DOI：10.1055/s-0036-1589045

  日期：2017.9

  A novel method of nucleophilic ring-opening of meso-epoxides with 4-aryl-NH-1,2,3-triazoles has been developed under metal-free conditions. The epoxide-ring opening process were carried out in the presence of organic bases (DABCO/Et3N) in acetonitrile at 85 °C to afford a regioisomeric mixture of trans-2-(4-aryl-2H-1,2,3-triazol-2-yl)cycloalkanols (2,4-disubstituted triazoles) as major adducts and trans-2-(4-aryl-1H-1,2,3-triazol-1-yl)cycloalkanols (1,4-disubstituted triazoles) as minor adducts in excellent combined chemical yields (isolated yield up to 99%).

  已经开发出一种新的无金属条件下，使用4-芳基-NH-1,2,3-三唑对中间环氧化合物进行亲核环开反应的方法。在乙腈中，加入有机碱（DABCO / Et3N）并在85°C下进行环氧化合物的环开过程，以得到顺式异构体混合物，其中trans-2-(4-芳基-2H-1,2,3-三唑-2-基)环己醇（2,4-二取代三唑）为主要产物，而trans-2-(4-芳基-1H-1,2,3-三唑-1-基)环己醇（1,4-二取代三唑）为次要产物，化学收率极高（分离收率高达99%）。