5-benzyloxy-1-phenyltetrazole | 180056-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-benzyloxy-1-phenyltetrazole
• 英文别名: 5-benzyloxy-1[H]-phenyltetrazole；1-phenyl-5-phenylmethoxytetrazole
• CAS: 180056-88-6
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: CAOAXGLSHHFALB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-1-phenyltetrazole 在 palladium on activated charcoal sodium hypophosphite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 生成 1-苯基-1,4-二氢-5H-四唑-5-酮 、 甲苯
  参考文献：
  名称：

  5-Benzyloxy-1-phenyltetrazole: catalytic transfer hydrogenolysis of benzyl ethers

  摘要：

  In contrast to the earlier reported inertness of 5-benzyloxy-1-phenyltetrazole, (1a), and 3-benzyloxy-1,2-benzisothiazole 1,1-dioxide, (2a), towards catalytic transfer hydrogenolysis in toluene/water solvent systems, it is now shown that simply changing the solvent to tetrahydrofuran/water leads to their rapid hydrogenolysis with formation of toluene. Compound (1a), C14H12N4O, has a short C-O ether bond to the tetrazole ring [1.3261(15) Angstrom] and a particularly long C-O bond to the benzyl group [1.4676(16) Angstrom], consistent with an activation of this longer bond by the strongly electronegative tetrazole unit.

  DOI：

  10.1107/s0108270199000141
• 作为产物：
  描述：

  5-氯-1-苯基-1H-四唑 、 苯甲醇 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到5-benzyloxy-1-phenyltetrazole
  参考文献：
  名称：

  金属辅助反应。第25部分。烯丙氧基四唑的均相和均相催化转移氢解反应，生成烯烃或烷烃

  摘要：

  使用非均相或均相钯催化剂和氢供体转移5-烯丙氧基-1-苯基四唑的氢解反应，导致烯丙氧基C-O键裂解产生链烷烃或烯烃和1-苯基四唑酮，具体取决于所使用的催化剂。

  DOI：

  10.1039/p19960001453

文献信息

• Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes
  作者：M. Lurdes S. Cristiano、Robert A. W. Johnstone、Peter J. Price

  DOI：10.1039/p19960001453

  日期：——

  Transfer hydrogenolysis of 5-allyloxy-l-phenyltetrazoles using either a heterogeneous or a homogeneous palladium catalyst and a hydrogen donor leads to cleavage of the allyloxy C–O bond to yield an alkane or an alkene and 1-phenyltetrazolone, depending on the catalyst used.

  使用非均相或均相钯催化剂和氢供体转移5-烯丙氧基-1-苯基四唑的氢解反应，导致烯丙氧基C-O键裂解产生链烷烃或烯烃和1-苯基四唑酮，具体取决于所使用的催化剂。
• Tetrazoles. 33. New method for obtaining functionally substituted tetrazoles
  作者：M. A. Gol'tsberg、G. I. Koldobskii

  DOI：10.1007/bf01169961

  日期：——
• 5-Benzyloxy-1-phenyltetrazole: catalytic transfer hydrogenolysis of benzyl ethers
  作者：A. F. Brigas、W. Clegg、R. A. W. Johnstone、R. F. Mendonca

  DOI：10.1107/s0108270199000141

  日期：1999.5.15

  In contrast to the earlier reported inertness of 5-benzyloxy-1-phenyltetrazole, (1a), and 3-benzyloxy-1,2-benzisothiazole 1,1-dioxide, (2a), towards catalytic transfer hydrogenolysis in toluene/water solvent systems, it is now shown that simply changing the solvent to tetrahydrofuran/water leads to their rapid hydrogenolysis with formation of toluene. Compound (1a), C14H12N4O, has a short C-O ether bond to the tetrazole ring [1.3261(15) Angstrom] and a particularly long C-O bond to the benzyl group [1.4676(16) Angstrom], consistent with an activation of this longer bond by the strongly electronegative tetrazole unit.