(benzotriazole-1-yl)methoxymethylbenzene | 73628-00-9

• 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: (benzotriazole-1-yl)methoxymethylbenzene
• 英文别名: 1-(methoxy-phenyl-methyl)-1H-benzotriazole；1-[Methoxy(phenyl)methyl]-1H-1,2,3-benzotriazole；1-[methoxy(phenyl)methyl]benzotriazole
• CAS: 73628-00-9
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: RVUCCEWTOJWLNG-UHFFFAOYSA-N

物化性质

• 沸点：
  150-155 °C(Press: 0.15 Torr)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (benzotriazole-1-yl)methoxymethylbenzene 在 盐酸 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-Methoxy-1-phenyl-pentan-3-one
  参考文献：
  名称：

  Synthesis of β-Alkoxy Ketones and α‘-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons

  摘要：

  1-(alpha-Alkoxyalkyl)benzotriazoles 1a-d add to phenyl vinyl ether to form key intermediates 4a-d, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7a-d, 9a-c, 11, 13, 15, and 18 in high yields. Subsequent hydrolysis of these compounds provides a novel high-yield acyl anion synthon approach for the synthesis of beta-alkoxy ketones 8 or alpha'-functionalized beta-alkoxy ketones 10, 12, 14, 16, and 19 by short procedures from readily available starting materials.

  DOI：

  10.1021/jo971630v
• 作为产物：
  描述：

  T406石油添加剂 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 22.0h， 生成 (benzotriazole-1-yl)methoxymethylbenzene
  参考文献：
  名称：

  唑类对苯甲醛及其二甲基缩醛的反应性。N，N'-重氮基苯基甲烷的合成

  摘要：

  在氯化锌的存在下，由吲唑和苯甲醛制备了一些1,1'-二吲唑基苯基甲烷。该反应是强烈依赖于基本的pK一个的唑类和仅少量的吡唑基衍生物可以通过此方法制备。通过使用苯甲醛二甲基乙缩醛可将该方法扩展至其他唑类。

  DOI：

  10.1016/s0040-4020(01)91435-8

文献信息

• Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers
  作者：Alan R. Katritzky、Stanislaw Rachwal、Bogumila Rachwal、Peter J. Steel

  DOI：10.1021/jo00044a030

  日期：1992.8

  1-(alpha-Alkoxybenzyl)benzotriazoles undergo reversible ionization in solution to a benzotriazolyl anion (Bt-) and carboxonium cations PhCH:O+R. These cations can attack the beta-carbon atom of enol ethers to give cation adducts which add the Bt- to form new alpha-(benzotriazol-1-yl)alkyl ethers in which the carbon chains are extended by an alpha-ethoxybenzyl group. Reactions of these adducts with Grignard reagents produce the corresponding 1,3-diethers in high yield. Reduction of the adducts with lithium aluminum hydride gives the corresponding diethers via substitution of the benzotriazolyl moiety with a hydrogen atom or 1-(3-alkoxyalkyl)benzotriazoles via substitution of the alpha-alkoxy group, depending on the reaction conditions and the nature of the adduct.
• Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila, Journal of the Chemical Society. Perkin transactions I, 1987, p. 791 - 798
  作者：Katritzky, Alan R.、Rachwal, Stanislaw、Rachwal, Bogumila

  DOI：——

  日期：——
• A New Method of Synthesis for Propargylic Amines and Ethers via Benzotriazole Derivatives Using Sodium Dialkynyldiethylaluminates
  作者：Jin Hee Ahn、Meyoung Ju Joung、Nung Min Yoon、Daniela C. Oniciu、Alan R. Katritzky

  DOI：10.1021/jo9814750

  日期：1999.1.1

  1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from Lithium acetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.
• Nucleofugality of the benzotriazole group in solvolysis
  作者：John P. Richard、R. W. Nagorski、Scott Rudich、Tina L. Amyes、Alan R. Katritzky、Adam P. Wells

  DOI：10.1021/jo00123a047

  日期：1995.9
• A Novel o-Iminophenyl Anion Route to Heterocycles and Ortho-Substituted Anilines
  作者：Alan R. Katritzky、Guifen Zhang、Jinlong Jiang、Peter J. Steel

  DOI：10.1021/jo00128a040

  日期：1995.11

  Ring opening of lithio derivatives of N-(alpha-alkoxyalkyl)benzotriazoles 9 and 22 and subsequent extrusion of nitrogen at -78 degrees C gave novel o-iminophenyl anions which enable synthetically useful preparations of ortho-substituted anilines (19 and 25) and of benzoheterocycles (14, 20, 21, 24, and 26).