1-azido-3-(4-phenyl-[1,2,3]triazol-1-yl)-propan-2-ol

• 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-azido-3-(4-phenyl-[1,2,3]triazol-1-yl)-propan-2-ol
• 英文别名: 3-azido-1-(4-phenyl-1H-1,2,3-triazol-1-yl)propan-2-ol；1-azido-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propan-2-ol；1-azido-3-(4-phenyltriazol-1-yl)propan-2-ol
• 化学式: C₁₁H₁₂N₆O
• 分子量: 244.256
• InChiKey: RLETUMWMKAWSML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-azido-3-(4-phenyl-[1,2,3]triazol-1-yl)-propan-2-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 6-(4-phenyl-1H-1,2,3-triazol-1-yl)-6,7-dihydro-4H-[1,2,3]triazolo-[5,1-c][1,4]oxazine
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w
• 作为产物：
  描述：

  苯乙炔 、 环氧氯丙烷 在 sodium azide 、 铜 作用下， 以 水 为溶剂， 反应 5.0h， 生成 1-azido-3-(4-phenyl-[1,2,3]triazol-1-yl)-propan-2-ol
  参考文献：
  名称：

  均匀的铜纳米颗粒，作为一种廉价高效的催化剂，可在水介质中合成新型β-羰基-1，2，3-三唑

  摘要：

  通过球磨制备铜纳米颗粒，作为一种有效，廉价的催化剂，用于在水中通过点击反应从叠氮醇合成β-羰基1、2、3-三唑。使用了多种原材料，例如叠氮化钠，苯甲酰溴，表氯醇和末端炔烃。在室温下，通过球磨与球粉重量比为50：1的球磨，可以完成NaBH 4存在下的CuO的完全还原。通过SEM，EDX，XRD和FT-IR对最终的铜纳米颗粒（Cu NPs）进行了表征。Cu NPs在室温下以短反应时间和高收率催化了β-羰基1、2、3-三唑的一锅三组分合成。该催化剂可以容易地回收并在几个连续的运行中重复使用。

  DOI：

  10.1007/s11164-019-03773-9

文献信息

• Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3+2] Cycloaddition:  Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif
  作者：Gullapalli Kumaraswamy、Kukkadapu Ankamma、Arigala Pitchaiah

  DOI：10.1021/jo701724f

  日期：2007.12.1

  [Graphics]A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.
• Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles
  作者：Kunj B. Mishra、Vinod K. Tiwari

  DOI：10.1021/jo500890w

  日期：2014.6.20

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.
• Uniform copper nanoparticles as an inexpensive and efficient catalyst for synthesis of novel β-carbonyl-1, 2, 3-triazoles in water medium
  作者：Hadi Esmaeili-Shahri、Hossein Eshghi、Jalil Lari、Seyyed Amin Rounaghi、Effat Esmaeili-Shahri

  DOI：10.1007/s11164-019-03773-9

  日期：2019.5

  prepared via ball milling for synthesis of β-carbonyl 1, 2, 3-triazoles from azido alcohol by click reaction in water. An extensive range of raw materials such as sodium azide, phenacyl bromide, epichlorohydrin, and terminal alkynes were used. Complete reduction of CuO in presence of NaBH4 was done via ball milling with a ball-to-powder weight ratio of 50:1 under air atmosphere at room temperature. The

  通过球磨制备铜纳米颗粒，作为一种有效，廉价的催化剂，用于在水中通过点击反应从叠氮醇合成β-羰基1、2、3-三唑。使用了多种原材料，例如叠氮化钠，苯甲酰溴，表氯醇和末端炔烃。在室温下，通过球磨与球粉重量比为50：1的球磨，可以完成NaBH 4存在下的CuO的完全还原。通过SEM，EDX，XRD和FT-IR对最终的铜纳米颗粒（Cu NPs）进行了表征。Cu NPs在室温下以短反应时间和高收率催化了β-羰基1、2、3-三唑的一锅三组分合成。该催化剂可以容易地回收并在几个连续的运行中重复使用。