N-[(p-methylphenyl)-telluromethyl]benzotriazole | 344549-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-[(p-methylphenyl)-telluromethyl]benzotriazole
• 英文别名: 1-[(4-Methylphenyl)tellanylmethyl]benzotriazole
• CAS: 344549-57-1
• 化学式: C₁₄H₁₃N₃Te
• 分子量: 350.877
• InChiKey: NOOSFSJJLOYCTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-二甲基苯基异腈 、 N-[(p-methylphenyl)-telluromethyl]benzotriazole 以 氘代苯 为溶剂， 反应 3.0h， 以78%的产率得到p-methylphenyl 2-(benzotriazol-1-yl)-N-(2,6-dimethylphenyl)-telluroacetimidate
  参考文献：
  名称：

  Synthetic and Theoretical Studies on Group-Transfer Imidoylation of Organotellurium Compounds. Remarkable Reactivity of Isonitriles in Comparison with Carbon Monoxide in Radical-Mediated Reactions

  摘要：

  Imidoylation of organotellurium compounds with isonitriles has been investigated in conjunction with the radical-mediated C1 homologation reaction by using CO and isonitriles. Carbon-centered radicals generated photochemically or thermally from organotellurium compounds react with isonitriles in a group-transfer manner to give the corresponding imidoylated products. Organotellurium compounds have been found to serve as effective precursors of a wide variety of stabilized radicals, namely benzyl, alpha -alkoxy, alpha -amino, and acyl radicals, which take part in the imidoylation with high efficiency. The reactions are compatible with various functional groups, and can be carried out in various solvents including environmentally benign water. The reactivity of isonitriles has been compared with that of CO through competition experiments, and the results indicate that isonitriles are superior to CO as radical accepters in reactions with stabilized radicals. The origin of the differences has been addressed in theoretical studies with density functional theory calculations using the B3LYP hybrid functional. The calculations suggest that both carbonylation and imidoylation proceed with low activation energies, and that there an virtually no differences in the kinetic sense, instead, it indicates that thermodynamic effects, namely differences in the stability of the acyl and the imidoyl radicals, control the overall course of the reactions.

  DOI：

  10.1021/ja003879r
• 作为产物：
  描述：

  1-(氯甲基)-1H-苯并三唑 、 4,4-二甲基二苯基二碲化物 在 六甲基磷酰三胺 、 samarium diiodide 作用下， 生成 N-[(p-methylphenyl)-telluromethyl]benzotriazole
  参考文献：
  名称：

  二碘化钐促进α-苯并三唑硒化物和碲化物的合成

  摘要：

  摘要 1-(苯并三唑-1-基)不对称二有机硒化物和碲化物是通过用SmI2促进的硒酸盐和碲酸盐阴离子取代1-(苯并三唑-1-基)-l-氯甲烷中的氯原子合成的。

  DOI：

  10.1080/00397919608004638

文献信息

• Synthesis of α-Benzotriazole Selenides and Tellurides Promoted by Samarium Diiodide
  作者：Jianqing Zhou、Weiliang Bao、Yongmin Zhang、Junquan Wang

  DOI：10.1080/00397919608004638

  日期：1996.9

  1-(Benzotriazol-1-yl) unsymmetrical diorganyl selenides and tellurides were synthesized via replacement of chlorine atom in 1-(benzotriazo-l-yl)-l-chloromethane with selenolate and tellurolate anions promoted by SmI2.

  摘要 1-(苯并三唑-1-基)不对称二有机硒化物和碲化物是通过用SmI2促进的硒酸盐和碲酸盐阴离子取代1-(苯并三唑-1-基)-l-氯甲烷中的氯原子合成的。
• Synthetic and Theoretical Studies on Group-Transfer Imidoylation of Organotellurium Compounds. Remarkable Reactivity of Isonitriles in Comparison with Carbon Monoxide in Radical-Mediated Reactions
  作者：Shigeru Yamago、Hiroshi Miyazoe、Ryuta Goto、Masahiro Hashidume、Takashi Sawazaki、Jun-ichi Yoshida

  DOI：10.1021/ja003879r

  日期：2001.4.1

  Imidoylation of organotellurium compounds with isonitriles has been investigated in conjunction with the radical-mediated C1 homologation reaction by using CO and isonitriles. Carbon-centered radicals generated photochemically or thermally from organotellurium compounds react with isonitriles in a group-transfer manner to give the corresponding imidoylated products. Organotellurium compounds have been found to serve as effective precursors of a wide variety of stabilized radicals, namely benzyl, alpha -alkoxy, alpha -amino, and acyl radicals, which take part in the imidoylation with high efficiency. The reactions are compatible with various functional groups, and can be carried out in various solvents including environmentally benign water. The reactivity of isonitriles has been compared with that of CO through competition experiments, and the results indicate that isonitriles are superior to CO as radical accepters in reactions with stabilized radicals. The origin of the differences has been addressed in theoretical studies with density functional theory calculations using the B3LYP hybrid functional. The calculations suggest that both carbonylation and imidoylation proceed with low activation energies, and that there an virtually no differences in the kinetic sense, instead, it indicates that thermodynamic effects, namely differences in the stability of the acyl and the imidoyl radicals, control the overall course of the reactions.