1-(methoxy-trimethylsilyl-methyl)-4-trimethylsilyl-1H-benzotriazole

• 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-(methoxy-trimethylsilyl-methyl)-4-trimethylsilyl-1H-benzotriazole
• 英文别名: [Methoxy-(4-trimethylsilylbenzotriazol-1-yl)methyl]-trimethylsilane
• 化学式: C₁₄H₂₅N₃OSi₂
• 分子量: 307.543
• InChiKey: FYMYRRVEUUIAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(氯甲基)-1H-苯并三唑 在 sodium 、 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， 生成 1-(methoxy-trimethylsilyl-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

文献信息

• Novel metallation of benzotriazoles and its utility in the synthesis of 4-substituted oxindoles
  作者：David P.M. Pleynet、Jonathan K. Dutton、M. Thornton-Pett、A.Peter Johnson

  DOI：10.1016/0040-4039(95)01221-3

  日期：1995.8

  Repeated metallation/silylation of 1-methoxymethylbenzotriazole 1 gives a high yield of the 4-tristrimethylsilyl benzotriazole derivative 5 which undergoes a high yielding fluoride-catalysed Peterson olefination reaction to give 1-(4-trimethylsilylbenzotriazolyl)-methoxymethylene adamantane 6b. Photolysis of 6b affords a remarkably strained iminoether 7b which can easily be converted to the corresponding

  1-methoxymethylbenzotriazole重复金属化/甲硅烷基化1给出了4- tristrimethylsilyl苯并三唑衍生物的高收率5而经历高产生氟化物催化Peterson烯反应，得到1-（4- trimethylsilylbenzotriazolyl）-methoxymethylene金刚烷6B。6b的光解作用可得到显着拉紧的亚氨基醚7b，该亚氨基醚7b可轻松转化为相应的羟吲哚9。