1-tert-butyl-1H-tetrazol-5-amine | 59772-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tert-butyl-1H-tetrazol-5-amine
• 英文别名: 1-tert-butyl-5-aminotetrazole；1-tert-butyl-1H-tetrazol-5-ylamine；1-Tert-butyltetrazol-5-amine
• CAS: 59772-93-9
• 化学式: C₅H₁₁N₅
• 分子量: 141.176
• InChiKey: FJBIEXNUZHJZSK-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• 沸点：
  274.1±23.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-1H-tetrazol-5-amine 、 硫酸二甲酯 以 乙腈 为溶剂， 反应 24.0h， 以83%的产率得到5-amino-1-tert-butyl-4-methyltetrazolium tetrafluoroborate
  参考文献：
  名称：

  Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1H-tetrazoles

  摘要：

  1,4-Dialkyl-5-(N-alkylimino)-4,5-dihydro-1H-tetrazoles were prepared in high yields by deprotonation with sodium hydride of 1,4-dialkyl-5-(N-alkylamino)tetrazolium salts that were adorned with two or three different alkyl groups, including methyl, trideuteriomethyl, and tert-butyl groups. Direct irradiation (lambda > 255 nm) at -60 degrees C yielded molecular nitrogen and mixtures of 1,2-dialkyl-3-(N-alkylimino)diaziridines (83-87%) along with carbodiimides (13-17%) arising by 1,3-dipolar cycloreversion. The missing 1,3-dipoles, alkyl azides, did not survive photolysis. Each member of a pair of isotopomers and of a pair of isomers, and an iminodihydrotetrazole, whose three nitrogens were tagged, yielded a characteristic mixture of three isomeric iminodiaziridines that allowed the mode of formation to be deduced. The results are interpreted in terms of photodenitrogenation of the iminodihydrotetrazoles to furnish diastereomeric singlet triazatrimethylenemethane diradicals that retain the inherited configurations before ring closure to iminodiaziridines, presumably in two steps via mono-orthogonal diradicals.

  DOI：

  10.1021/jo702697f
• 作为产物：
  描述：

  tert-butyl cyanamide 在 sodium azide 、 氯化铵 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-tert-butyl-1H-tetrazol-5-amine 、 N-tert-butyl-2H-tetrazol-5-amine
  参考文献：
  名称：

  Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1H-tetrazoles

  摘要：

  1,4-Dialkyl-5-(N-alkylimino)-4,5-dihydro-1H-tetrazoles were prepared in high yields by deprotonation with sodium hydride of 1,4-dialkyl-5-(N-alkylamino)tetrazolium salts that were adorned with two or three different alkyl groups, including methyl, trideuteriomethyl, and tert-butyl groups. Direct irradiation (lambda > 255 nm) at -60 degrees C yielded molecular nitrogen and mixtures of 1,2-dialkyl-3-(N-alkylimino)diaziridines (83-87%) along with carbodiimides (13-17%) arising by 1,3-dipolar cycloreversion. The missing 1,3-dipoles, alkyl azides, did not survive photolysis. Each member of a pair of isotopomers and of a pair of isomers, and an iminodihydrotetrazole, whose three nitrogens were tagged, yielded a characteristic mixture of three isomeric iminodiaziridines that allowed the mode of formation to be deduced. The results are interpreted in terms of photodenitrogenation of the iminodihydrotetrazoles to furnish diastereomeric singlet triazatrimethylenemethane diradicals that retain the inherited configurations before ring closure to iminodiaziridines, presumably in two steps via mono-orthogonal diradicals.

  DOI：

  10.1021/jo702697f

文献信息

• Adamantylazoles: XIV. Acid-catalyzed alkylation of 5-aminotetrazoles with tertiary alcohols
  作者：A. V. Logvinov、I. N. Polyakova、E. L. Golod

  DOI：10.1134/s1070363210110228

  日期：2010.11

  Alkylation of 5-aminotetrazole with tert-butyl alcohol or adamantan-1-ol in sulfuric acid gave a mixture of isomeric N 1- and N 2-alkyl derivatives, as well as 1,3-dialkyl-5-aminotetrazolium salt. Adamantylation of 1-substituted 5-aminotetrazoles led to the formation of mixtures of 1,3- and 1,4-disubstituted 5-aminotetrazolium salts which can be converted into the corresponding free bases.

  将5-氨基四唑与叔丁醇或金刚烷-1-醇在硫酸中烷基化，得到异构的N 1-和N 2-烷基衍生物以及1,3-二烷基-5-氨基四唑盐的混合物。1-取代的5-氨基四唑的金刚烷基化导致形成1,3-和1,4-二取代的5-氨基四唑盐的混合物，这些盐可以转化为相应的游离碱。
• HENRY R. A., J. HETEROCYCL. CHEM. <JHTC-AD>, 1976, 13, NO 2, 391-392
  作者：HENRY R. A.

  DOI：——

  日期：——
• Iminodiaziridines by Regio- and Stereoselective Cyclization of Diastereomeric Singlet Triazatrimethylenemethane Diradicals Generated Through Photolysis of 5-Imino-4,5-dihydro-1<i>H</i>-tetrazoles
  作者：Helmut Quast、Lothar W. Bieber

  DOI：10.1021/jo702697f

  日期：2008.5.1

  1,4-Dialkyl-5-(N-alkylimino)-4,5-dihydro-1H-tetrazoles were prepared in high yields by deprotonation with sodium hydride of 1,4-dialkyl-5-(N-alkylamino)tetrazolium salts that were adorned with two or three different alkyl groups, including methyl, trideuteriomethyl, and tert-butyl groups. Direct irradiation (lambda > 255 nm) at -60 degrees C yielded molecular nitrogen and mixtures of 1,2-dialkyl-3-(N-alkylimino)diaziridines (83-87%) along with carbodiimides (13-17%) arising by 1,3-dipolar cycloreversion. The missing 1,3-dipoles, alkyl azides, did not survive photolysis. Each member of a pair of isotopomers and of a pair of isomers, and an iminodihydrotetrazole, whose three nitrogens were tagged, yielded a characteristic mixture of three isomeric iminodiaziridines that allowed the mode of formation to be deduced. The results are interpreted in terms of photodenitrogenation of the iminodihydrotetrazoles to furnish diastereomeric singlet triazatrimethylenemethane diradicals that retain the inherited configurations before ring closure to iminodiaziridines, presumably in two steps via mono-orthogonal diradicals.