2-methoxycarbonyl-5-(2,6-dimethylphenoxy)tetrazole | 311762-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxycarbonyl-5-(2,6-dimethylphenoxy)tetrazole
• 英文别名: Methyl 5-(2,6-dimethylphenoxy)tetrazole-2-carboxylate；methyl 5-(2,6-dimethylphenoxy)tetrazole-2-carboxylate
• CAS: 311762-18-2
• 化学式: C₁₁H₁₂N₄O₃
• 分子量: 248.241
• InChiKey: IHPOROOYCXBCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxycarbonyl-5-(2,6-dimethylphenoxy)tetrazole 在 三氯化铝 、 1,3,5-三甲氧基苯 作用下， 反应 0.33h， 生成 、
  参考文献：
  名称：

  A one-pot synthesis and X-ray crystallographic and computational analyses of methyl-2,4-dimethoxysalicylate — a potential anti-tumour agent

  摘要：

  本文研究了2-甲氧羰基-5-(4'-硝基苯氧基)四唑（1a）与富电子芳香化合物（甲氧基苯、N,N-二甲基苯胺、1,4-二甲氧基苯和1,3,5-三甲氧基苯）在无溶剂或极性溶剂（DMSO、DMF和CH3CN）中的热脱羧反应。将1a、1,3,5-三甲氧基苯和Lewis酸（AlCl3）混合物的固相热分解产物为甲基-2,4-二甲氧基水杨酸酯（8），而不是预期的2,4,6-三甲氧基苯甲酸。8的X射线结构显示了羰基氧原子与Me和OH基团的氢键内部作用。实测pKa值为6.8，与使用[C=O···H···O]氢键距离估计的值6.4相符。关键词：抗肿瘤、新型合成、X射线结构、氢键、计算分析。

  DOI：

  10.1139/v04-113
• 作为产物：
  描述：

  5-(2,6-dimethylphenoxy)tetrazole 、 氯甲酸甲酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 以94%的产率得到2-methoxycarbonyl-5-(2,6-dimethylphenoxy)tetrazole
  参考文献：
  名称：

  Equilibria of the 5-Substituted-1,2-acylated Tetrazoles and Imidoyl Azides

  摘要：

  Equilibrium of acylated-5-alkyloxy (aryloxy) tetrazoles and acylated-imidoyl azides was measured by (1)H NMR and/or IR spectroscopy. In nonpolar solvents the relatively weakly electron-withdrawing acyl group (CO(2)CH(3)) favored acylation at the a-position of the 5-substituted tetrazoles. Moderately electron-withdrawing groups (CO(2)CH(2)CCl(3), CO(2)CCl(3)) move the equilibrium to the side of 1-acyl-5-substituted tetrazole. Strong electron-withdrawing groups (CN, SO(2)CH(3), SO(2)CF(3)) favored the formation of the azide. The rate of isomerization of tetrazoles and the azide increases at higher concentrations and polarity of the solvent. In solid phase or in the nonpolar solvent (diethyl ether), only one of the three isomers is present, its structure depending on the nature of the substituents at the 1 or 2 positions of tetrazoles.

  DOI：

  10.1021/jo000267g

文献信息

• Equilibria of the 5-Substituted-1,2-acylated Tetrazoles and Imidoyl Azides
  作者：Hossein A. Dabbagh、Walter Lwowski

  DOI：10.1021/jo000267g

  日期：2000.11.1

  Equilibrium of acylated-5-alkyloxy (aryloxy) tetrazoles and acylated-imidoyl azides was measured by (1)H NMR and/or IR spectroscopy. In nonpolar solvents the relatively weakly electron-withdrawing acyl group (CO(2)CH(3)) favored acylation at the a-position of the 5-substituted tetrazoles. Moderately electron-withdrawing groups (CO(2)CH(2)CCl(3), CO(2)CCl(3)) move the equilibrium to the side of 1-acyl-5-substituted tetrazole. Strong electron-withdrawing groups (CN, SO(2)CH(3), SO(2)CF(3)) favored the formation of the azide. The rate of isomerization of tetrazoles and the azide increases at higher concentrations and polarity of the solvent. In solid phase or in the nonpolar solvent (diethyl ether), only one of the three isomers is present, its structure depending on the nature of the substituents at the 1 or 2 positions of tetrazoles.
• A one-pot synthesis and X-ray crystallographic and computational analyses of methyl-2,4-dimethoxysalicylate — a potential anti-tumour agent
  作者：Hossein A Dabbagh、Nader Noroozi-Pesyan、Brian O Patrick、Brian R James

  DOI：10.1139/v04-113

  日期：2004.7.1

  The thermal decarboxylation of 2-methoxycarbonyl-5-(4′-nitrophen-oxy)tetrazole (1a) with the electron-rich, aromatic compounds (anisole, N,N-dimethylaniline, 1,4-dimethoxybenzene, and 1,3,5-trimethoxybenzene), neat or in polar solvents (DMSO, DMF, and CH₃CN), is investigated. The solid phase thermal decomposition of a mixture of 1a, 1,3,5-trimethoxybenzene, and a Lewis acid (AlCl₃) produces methyl-2,4-dimethoxysalicylate (8) in good yield, instead of the expected 2,4,6-trimethoxybenzoic acid. The X-ray structure of 8 shows intramolecular hydrogen bonds between the carbonyl oxygen and hydrogens of Me and OH groups. A measured pK_a value of 6.8 compares well with a value of 6.4 estimated using the [C=O···H···O] hydrogen bond distances.Key words: anti–tumor, novel synthesis, X-ray structure, hydrogen bonds, computational analysis.

  本文研究了2-甲氧羰基-5-(4'-硝基苯氧基)四唑（1a）与富电子芳香化合物（甲氧基苯、N,N-二甲基苯胺、1,4-二甲氧基苯和1,3,5-三甲氧基苯）在无溶剂或极性溶剂（DMSO、DMF和CH3CN）中的热脱羧反应。将1a、1,3,5-三甲氧基苯和Lewis酸（AlCl3）混合物的固相热分解产物为甲基-2,4-二甲氧基水杨酸酯（8），而不是预期的2,4,6-三甲氧基苯甲酸。8的X射线结构显示了羰基氧原子与Me和OH基团的氢键内部作用。实测pKa值为6.8，与使用[C=O···H···O]氢键距离估计的值6.4相符。关键词：抗肿瘤、新型合成、X射线结构、氢键、计算分析。