dimethyl 1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazole-4,5-dicarboxylate | 869895-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazole-4,5-dicarboxylate
• 英文别名: dimethyl 1-(2-oxo-2-phenylethyl)-1H-1,2,3-triazole-4,5-dicarboxylate；dimethyl 1-phenacyltriazole-4,5-dicarboxylate
• CAS: 869895-64-7
• 化学式: C₁₄H₁₃N₃O₅
• mdl: MFCD22549280
• 分子量: 303.274
• InChiKey: UXIKHYQVKAZWBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazole-4,5-dicarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.05h， 以98.5%的产率得到dimethyl 1-(2-hydroxy-2-phenylethyl)-1H-1,2,3-triazole-4,5-dicarboxylate
  参考文献：
  名称：

  1H-1,2,3-三唑二酯的区域选择性还原

  摘要：

  区域选择性反应可以在合成有机化学中发挥关键作用。已发现硼氢化钠对几种 1-取代的 1,2,3-三唑 4,5-二酯的还原具有区域选择性，其中 C(5) 酯基团比 C(4) 酯基团对还原更具反应性. 硼氢化钠的量和还原所需的反应时间因 N(1)-取代基而异。N(1)-取代基上β-羟基的存在被认为对C(5)酯基团的还原具有速率增强作用。区域选择性减少归因于 1,2,3-三唑的 C(5) 和 C(5) 酯羰基碳的较低电子密度，在涉及分子内氢键的情况下进一步降低。

  DOI：

  10.3390/molecules26185589
• 作为产物：
  描述：

  苯乙酮 在 aluminum (III) chloride 、 sodium azide 、 溴 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 24.02h， 生成 dimethyl 1-(2-oxo-2-phenylethyl)-1H-[1,2,3]triazole-4,5-dicarboxylate
  参考文献：
  名称：

  Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis

  摘要：

  Efficient and rapid synthesis of 1,2,3-triazole derivatives has been achieved via Huisgen's 1,3-dipolar cycloaddition between alkyl/arylazides and diethyl/dimethyl acetylenedicarboxylate in excellent yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the prevailing time-consuming solution phase protocols and affords the triazoles just in 1-3 min. In vitro antitubercular activity of these triazoles was screened against Mycobacterium tuberculosis H(37)Rv strain. Four of the compounds showed MIC in the range of 1.56-3.13 mu g/mL proving their potential activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.048

文献信息

• Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis
  作者：Poovan Shanmugavelan、Sangaraiah Nagarajan、Murugan Sathishkumar、Alagusundaram Ponnuswamy、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2011.10.048

  日期：2011.12

  Efficient and rapid synthesis of 1,2,3-triazole derivatives has been achieved via Huisgen's 1,3-dipolar cycloaddition between alkyl/arylazides and diethyl/dimethyl acetylenedicarboxylate in excellent yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the prevailing time-consuming solution phase protocols and affords the triazoles just in 1-3 min. In vitro antitubercular activity of these triazoles was screened against Mycobacterium tuberculosis H(37)Rv strain. Four of the compounds showed MIC in the range of 1.56-3.13 mu g/mL proving their potential activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Regioselective Reduction of 1H-1,2,3-Triazole Diesters
  作者：Christopher R. Butler、Justin Bendesky、Allen Milton Schoffstall

  DOI：10.3390/molecules26185589

  日期：——

  Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on

  区域选择性反应可以在合成有机化学中发挥关键作用。已发现硼氢化钠对几种 1-取代的 1,2,3-三唑 4,5-二酯的还原具有区域选择性，其中 C(5) 酯基团比 C(4) 酯基团对还原更具反应性. 硼氢化钠的量和还原所需的反应时间因 N(1)-取代基而异。N(1)-取代基上β-羟基的存在被认为对C(5)酯基团的还原具有速率增强作用。区域选择性减少归因于 1,2,3-三唑的 C(5) 和 C(5) 酯羰基碳的较低电子密度，在涉及分子内氢键的情况下进一步降低。