dimethyl 1-(2-methoxy-2-oxoethyl)-1H-1,2,3-triazole-4,5-dicarboxylate | 561297-30-1

• 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: dimethyl 1-(2-methoxy-2-oxoethyl)-1H-1,2,3-triazole-4,5-dicarboxylate
• 英文别名: 1-methoxycarbonylmethyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester；1-Methoxycarbonylmethyl-1H-[1,2,3]triazol-4,5-dicarbonsaeure-dimethylester；Dimethyl 1-(2-methoxy-2-oxo-ethyl)triazole-4,5-dicarboxylate；dimethyl 1-(2-methoxy-2-oxoethyl)triazole-4,5-dicarboxylate
• CAS: 561297-30-1
• 化学式: C₉H₁₁N₃O₆
• 分子量: 257.203
• InChiKey: FHOYLGDTZSMDFA-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±52.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(2-methoxy-2-oxoethyl)-1H-1,2,3-triazole-4,5-dicarboxylate 在 一水合肼 作用下， 生成 1-hydrazinocarbonylmethyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dihydrazide
  参考文献：
  名称：

  Curtius; Klavehn, Journal fur praktische Chemie (Leipzig 1954), 1930, vol. <2>125, p. 498,517

  摘要：

  DOI：
• 作为产物：
  描述：

  2-叠氮基乙酸甲酯 、 丁炔二酸二甲酯 反应 0.03h， 生成 dimethyl 1-(2-methoxy-2-oxoethyl)-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

• Preparation, Characterization, and Reactivity of Azido Complex Containing a Tp(^<i>t</i>BuNC)(PPh₃)Ru Fragment and Ruthenium-Catalyzed Cycloaddition of Organic Azides with Alkynes in Organic and Aqueous Media
  作者：Yih-Hsing Lo、Tsang-Hsiu Wang、Chia-Yi Lee、Ying-Hsuan Feng

  DOI：10.1021/om300687a

  日期：2012.10.8

  five-membered cyclic oxycarbene complex (PPh3)[Ru]═C4H6O}+ (11). Several cationic imine complexes (tBuNC)[Ru]-(NH═CHR′)}+ (12a, R′ = H; 12b, R′ = CH3; 12c, R′ = Ph) are formed by the reaction of RCH2X with 2. If the reaction of 2 with CH3I is carried out at 35 °C for 24 h, (tBuNC)[Ru]-I (13) could be isolated. Preliminary results on the catalytic activity of 2 are also presented. Complex 2 catalyzes cycloaddition

  用过量的叠氮化钠处理TpRu络合物（PPh 3）[Ru] -Cl（1，[Ru] = Tp（t BuNC）Ru）得到黄色钌叠氮基络合物（PPh 3）[Ru] -N 3（2）。所述三唑合复合物（PPH 3）的[Ru] -N 3 Ç 2（R）2（图3a，R =甲基;图3b，R = ET）经由合成[3 + 2]环加成的2用RO 2 CC≡CCO 2 R.这些triazolato配合物的完整表征阐明了结构，并确定了加成产物的N（2）键类型。的烷基化3a与有机溴化物引起Ru–N键断裂，并提供1,4,5-三取代的三唑。此外，除了CS的2至2产生热不稳定thiothiatriazolate（PPH 3）的[Ru] -N 3 CS（S）（5），其转换成异硫氰酸酯复合物（PPH 3）的[Ru] -NCS（6）和（t BuNC）[Ru] -NCS（7）。其他试剂也可与2反应，但产物不是由[3 + 2]环加成反应产生的。在H
• General Solution to the Synthesis of <i>N</i>-2-Substituted 1,2,3-Triazoles
  作者：Xiao-jun Wang、Li Zhang、Dhileepkumar Krishnamurthy、Chris H. Senanayake、Peter Wipf

  DOI：10.1021/ol101965a

  日期：2010.10.15

  The regioselective N-alkylation of 1,2,3-triazoles 1-6 was studied Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5-trimethylsilyl-1,2,3-triazoles These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10-15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds
• 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.
• Curtius; Klavehn, Journal fur praktische Chemie (Leipzig 1954), 1930, vol. <2>125, p. 498,517
  作者：Curtius、Klavehn

  DOI：——

  日期：——