1-(benzotriazol-1-yl)-1-phenoxy-1-trimethylsilylmethane | 155510-96-6

• 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: 1-(benzotriazol-1-yl)-1-phenoxy-1-trimethylsilylmethane
• 英文别名: 1-(phenoxy-trimethylsilyl-methyl)-1H-benzotriazole；1-[Phenoxy(trimethylsilyl)methyl]-1H-1,2,3-benzotriazole；[benzotriazol-1-yl(phenoxy)methyl]-trimethylsilane
• CAS: 155510-96-6
• 化学式: C₁₆H₁₉N₃OSi
• 分子量: 297.432
• InChiKey: RROSOUKXERTOSL-UHFFFAOYSA-N

物化性质

• 沸点：
  436.1±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzotriazol-1-yl)-1-phenoxy-1-trimethylsilylmethane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-(phenoxy-bistrimethylsilyl-methyl)-4-trimethylsilyl-1H-benzotriazole
  参考文献：
  名称：

  A general synthesis of 1-(1-alkenyl)benzotriazoles

  摘要：

  1-Methyl, 1-(alkoxymethyl) and 1-(trimethylsilylmethyl)benzotriazoles are metallated at the alpha-carbon. Trapping of the resulting metallated species with chlorotrimethylsilane gives compounds which undergo Peterson olefination even with hindered ketones. In some cases, metallation at the 4-position of the benzotriazole is observed. An exhaustive metallation/silylation sequence gives 4-trimethylsilyl substituted 1-benzotriazoles in good yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00690-0
• 作为产物：
  描述：

  1-(氯甲基)-1H-苯并三唑 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(benzotriazol-1-yl)-1-phenoxy-1-trimethylsilylmethane
  参考文献：
  名称：

  A general synthesis of 1-(1-alkenyl)benzotriazoles

  摘要：

  1-Methyl, 1-(alkoxymethyl) and 1-(trimethylsilylmethyl)benzotriazoles are metallated at the alpha-carbon. Trapping of the resulting metallated species with chlorotrimethylsilane gives compounds which undergo Peterson olefination even with hindered ketones. In some cases, metallation at the 4-position of the benzotriazole is observed. An exhaustive metallation/silylation sequence gives 4-trimethylsilyl substituted 1-benzotriazoles in good yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00690-0

文献信息

• A total synthesis of gelsemine: oxindole spiroannelation
  作者：Jonathan K. Dutton、Robert W. Steel、Andrew S. Tasker、Velimir Popsavin、A. Peter Johnson

  DOI：10.1039/c39940000765

  日期：——

  Photolysis of alkoxy-substituted-1-alkenylbenzotriazoles provides a new route to spiro-oxindoles which has been utilised in a total synthesis of gelsemine.

  烷氧基取代的-1-烯基苯并三唑的光解提供了一条制备螺吲哚的新路线，该路线已用于钩吻碱的全合成。
• Novel Access to Thioacylsilanes with Benzotriazole-Mediated Methodology
  作者：Alessandro Degl'Innocenti、Antonella Capperucci、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1021/jo0011585

  日期：2000.12.1