5-p-nitrophenoxytetrazole | 6773-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-p-nitrophenoxytetrazole
• 英文别名: 5-(4-nitrophenoxy)tetrazole；5-(p-Nitro-phenoxy)-tetrazol；5-(4-nitro-phenoxy)-1H-tetrazole；5-(4-nitrophenoxy)-2H-tetrazole
• CAS: 6773-32-6
• 化学式: C₇H₅N₅O₃
• 分子量: 207.148
• InChiKey: FRNBDRFJHOHNMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-p-nitrophenoxytetrazole 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到N^I-(4-methylbenzenesulfonyl)(4-nitrophenoxy)imidoyl azide
  参考文献：
  名称：

  一种简便有效的合成芳氧基亚氨酰叠氮化物的方法

  摘要：

  以定量收率引入了新的芳氧基亚氨酰基叠氮化物的简便有效的合成。

  DOI：

  10.3184/030823400103165653
• 作为产物：
  描述：

  P-硝基苯基氰酸酯 在 sodium azide 、 cobalt ferrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 以81%的产率得到5-p-nitrophenoxytetrazole
  参考文献：
  名称：

  CoFe₂O₄ Nanoparticles as a Magnetically Recoverable and Reusable Catalyst for the Synthesis of Arylaminotetrazoles and 5-aryloxytetrazoles

  摘要：

  以纳米 CoFe2O4 作为可重复使用的高效异相催化剂，描述了一种从芳基氰化物或犬牙交错化合物合成 5-芳基氨基-1H-四唑（异构体 A）或 1-芳基-5-氨基-1H-四唑（异构体 B）和 5-芳氧基四唑的高效直接方法。异构体 A 是由芳基环上带有电子吸收取代基的芳基氰化物制得的，而异构体 B 则是由电子释放基团制得的。这种方法的显著优点是产率高、无需使用危险和有害的苯甲酸、操作步骤简单以及催化剂可回收和重复使用。

  DOI：

  10.3184/174751914x13871210981307

文献信息

• Reaction of 5-Aryloxytetrazoles with Dimethyl Sulfoxide and DMSO-Acetic Anhydride. Structure and Quantum-Chemical Calculations of 1-Methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole
  作者：H. A. Dabbagh、N. Noroozi Pesyan、A. Bagheri、S. Takemo、H. Hayashi

  DOI：10.1007/s11178-005-0293-9

  日期：2005.7

  Decomposition of methyl 5-(4-nitrophenoxy)tetrazole-2-carboxylate in dimethyl sulfoxide at room temperature yields a mixture of 1-methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole, 1- and 2-methyl-5-(4-nitrophenoxy)tetrazoles, and 5-(4-nitrophenoxy)tetrazole. Methyl 5-aryloxytetrazole-2-carboxylates containing electron-donor substituents in the aryloxy group do not give rise to the corresponding products under analogous conditions. The reactions of 5-aryloxytetrazoles [Ar = 4-O2NC6H4, C6H5, 2,6-(MeO)2C6H3] with dimethyl sulfoxide in the presence of acetic anhydride lead to mixtures of 1- and 2-methylsulfanylmethyl-5-aryloxytetrazoles whose yield and ratio depend on the substituent in the aryloxy group. The structure of 1-methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole was studied by X-ray analysis, two-dimensional NMR spectroscopy (HSQC, HMBC, NOESY), and quantum-chemical methods (ab initio, AM1, PM3). A highly selective procedure was developed for the synthesis of 5-(4-nitrophenoxy)tetrazole.

  在室温下，甲基5-(4-硝基苯氧基)四唑-2-羧酸酯在二甲基亚砜中的分解反应生成1-甲硫基甲基-5-(4-硝基苯氧基)四唑、1-和2-甲基-5-(4-硝基苯氧基)四唑以及5-(4-硝基苯氧基)四唑的混合物。含有供电子取代基的芳氧基团的甲基5-芳氧基四唑-2-羧酸酯在类似条件下不会生成相应的产物。在乙酸酐存在下，5-芳氧基四唑[Ar = 4-O2NC6H4, C6H5, 2,6-(MeO)2C6H3]与二甲基亚砜的反应生成1-和2-甲硫基甲基-5-芳氧基四唑的混合物，其产率和比例取决于芳氧基团上的取代基。通过X射线分析、二维核磁共振光谱（HSQC, HMBC, NOESY）和量子化学方法（从头计算法，AM1, PM3）研究了1-甲硫基甲基-5-(4-硝基苯氧基)四唑的结构。开发了一种高度选择性的5-(4-硝基苯氧基)四唑合成方法。
• 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。
• ——
  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.
• Dabbagh, Hossein A.; Bagheri, Ali, Journal of Chemical Research, 2005, # 3, p. 202 - 204
  作者：Dabbagh, Hossein A.、Bagheri, Ali

  DOI：——

  日期：——