3-(4-n-hexyl-1H-1,2,3-triazol-1yl)dihydrofuran-2(3H)-one | 1393738-75-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-n-hexyl-1H-1,2,3-triazol-1yl)dihydrofuran-2(3H)-one
• 英文别名: 3-(4-Hexyltriazol-1-yl)oxolan-2-one
• CAS: 1393738-75-4
• 化学式: C₁₂H₁₉N₃O₂
• 分子量: 237.302
• InChiKey: ZODBHXQHQRSAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-辛炔 、 3-azidodihydrofuran-2(3H)-one 在 2-{4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl}cyclohexan-1-ol 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以89%的产率得到3-(4-n-hexyl-1H-1,2,3-triazol-1yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  一种新型的水溶性配体，可有效催化铜催化脂肪族叠氮化物和炔烃的惠斯根环加成反应

  摘要：

  使用新型水溶性催化配体2- {4-[（（二甲基氨基）甲基] -1,2,3-三唑-1-基}环己基- 1-ol（AMTC）。测试了一系列脂族和芳族底物，并将其与众所周知的三（三唑）胺配体（TBTA和THPTA）进行了比较。还研究了溶剂组成的影响。

  DOI：

  10.1016/j.tetlet.2015.09.110

文献信息

• [EN] DERIVATIVES OF 1,2,3-TRIAZOLYL CYCLOHEXAN-1-OL AND ITS USE<br/>[FR] DÉRIVÉS DE 1,2,3-TRIAZOLYLE CYCLOHEXAN-1-OL ET LEUR UTILISATION
  申请人：UNIV JAGIELLONSKI

  公开号：WO2016200283A1

  公开（公告）日：2016-12-15

  1,2,3-triazolyl cyclohexanol derivatives have been disclosed and their use as ligands accelerating the copper(I)-catalyzed azide-alkyne cycloaddition and the zinc(II)-catalyzed azide-nitrile cycloaddition.

  已经披露了1,2,3-三唑基环己醇衍生物，并且它们被用作加速铜(I)催化的叠氮-炔烃环加成和锌(II)催化的叠氮-腈环加成的配体。
• Synthesis and evaluation of the quorum sensing inhibitory effect of substituted triazolyldihydrofuranones
  作者：Gilles Brackman、Martijn Risseeuw、Shari Celen、Paul Cos、Louis Maes、Hans J. Nelis、Serge Van Calenbergh、Tom Coenye

  DOI：10.1016/j.bmc.2012.06.009

  日期：2012.8

  Acylhomoserine lactone (AHL) analogues in which the amide function is replaced by a triazole group were synthesized and evaluated for their effect on quorum sensing (QS) and biofilm formation in Burkholderia cenocepacia and Pseudomonas aeruginosa. In addition, the influence of the length of the acyl-mimicking chain was investigated. The compounds showed selectivity between two different AHL QS systems. 3-(1H-1,2,3-Triazol-1-yl)dihydrofuran-2(3H)-ones, in which the 4-substituent best resembled the acyl chain of the native AHL molecule exhibited significant QS agonistic and antagonistic activities. Replacing this aliphatic substituent by a phenyl-containing moiety resulted in active inhibitors of QS. The most active compounds showed biofilm inhibitory as well as biofilm eradicating activities in both test organisms. (C) 2012 Elsevier Ltd. All rights reserved.
• A new water-soluble ligand for efficient copper-catalyzed Huisgen cycloaddition of aliphatic azides and alkynes
  作者：Przemysław W. Szafrański、Patryk Kasza、Marek T. Cegła

  DOI：10.1016/j.tetlet.2015.09.110

  日期：2015.11

  Efficient procedures for the copper-catalyzed Huisgen cycloaddition reaction in aqueous media were developed using a novel water-soluble catalytic ligand, 2-4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl}cyclohexan-1-ol (AMTC). A series of aliphatic and aromatic substrates were tested and compared to the well-known tris(triazole)amine ligands (TBTA and THPTA). The effect of solvent composition was also

  使用新型水溶性催化配体2- 4-[（（二甲基氨基）甲基] -1,2,3-三唑-1-基}环己基- 1-ol（AMTC）。测试了一系列脂族和芳族底物，并将其与众所周知的三（三唑）胺配体（TBTA和THPTA）进行了比较。还研究了溶剂组成的影响。