Methyl 5-(2,4,6-trimethylphenoxy)tetrazole-2-carboxylate | 320603-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 5-(2,4,6-trimethylphenoxy)tetrazole-2-carboxylate
• 英文别名: methyl 5-(2,4,6-trimethylphenoxy)tetrazole-2-carboxylate
• CAS: 320603-41-6
• 化学式: C₁₂H₁₄N₄O₃
• 分子量: 262.268
• InChiKey: QZLXRVDDQMORCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  Methyl 5-(2,4,6-trimethylphenoxy)tetrazole-2-carboxylate 以 氘代二甲亚砜 、 氘代氯仿 为溶剂， 生成
  参考文献：
  名称：

  摘要：

  The kinetics and mechanism of the N-2-N-1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO,) were studied by H-1 NMR spectroscopy in a DMSO-d(6)-CDCl3 mixture (25: 75). The rate of isomerization of the N-2-isomer into N-1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of ln(k(x)/k(H)) for the isomerization showed a good correlation with sigma(-) values (p(-) = 1.33, r = 0.965). A poor correlation with sigma values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AMI quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.

  DOI：

  10.1023/a:1013947228772
• 作为产物：
  描述：

  氯甲酸甲酯 、 5-(mesityloxy)-1H-tetrazole 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到Methyl 5-(2,4,6-trimethylphenoxy)tetrazole-2-carboxylate
  参考文献：
  名称：

  摘要：

  The kinetics and mechanism of the N-2-N-1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO,) were studied by H-1 NMR spectroscopy in a DMSO-d(6)-CDCl3 mixture (25: 75). The rate of isomerization of the N-2-isomer into N-1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of ln(k(x)/k(H)) for the isomerization showed a good correlation with sigma(-) values (p(-) = 1.33, r = 0.965). A poor correlation with sigma values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AMI quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.

  DOI：

  10.1023/a:1013947228772

文献信息

• Dabbagh; Mansoori; Jafary, Journal of Chemical Research - Part S, 2000, # 9, p. 442 - 445
  作者：Dabbagh、Mansoori、Jafary、Rostami

  DOI：——

  日期：——
• ——
  作者：H. A. Dabbagh、Ya. Mansoori

  DOI：10.1023/a:1013947228772

  日期：——

  The kinetics and mechanism of the N-2-N-1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO,) were studied by H-1 NMR spectroscopy in a DMSO-d(6)-CDCl3 mixture (25: 75). The rate of isomerization of the N-2-isomer into N-1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of ln(k(x)/k(H)) for the isomerization showed a good correlation with sigma(-) values (p(-) = 1.33, r = 0.965). A poor correlation with sigma values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AMI quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.