1-(Ethoxy-phenyl-methyl)-1H-benzotriazole | 172264-94-7

• 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-(Ethoxy-phenyl-methyl)-1H-benzotriazole
• 英文别名: 1-(Ethoxyphenylmethyl)-1H-benzotriazole；1-[ethoxy(phenyl)methyl]benzotriazole
• CAS: 172264-94-7
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: PKTKOAGPIFVJDD-UHFFFAOYSA-N

物化性质

• 沸点：
  412.3±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-(Ethoxy-phenyl-methyl)-1H-benzotriazole 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 水 为溶剂， 反应 0.25h， 生成 3-chloro-4-nitrobenzophenone
  参考文献：
  名称：

  Reactions of 1-(Benzotriazol-1-yl)-1-phenoxyalkane and (Benzotriazol-1-yl)ethoxyphenylmethane Anions with Nitroarenes: a New Approach to Alkyl and Aryl p-Nitroaryl Ketones

  摘要：

  通过对非功能化硝基苯和苯并三氮唑稳定化碳负离子的反应，可选择性地制备p-硝基芳基烷基酮和p-硝基芳基苯基酮。

  DOI：

  10.1039/a900891h
• 作为产物：
  描述：

  T406石油添加剂 、 苯甲醛二乙缩醛 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(Ethoxy-phenyl-methyl)-1H-benzotriazole
  参考文献：
  名称：

  Additions of 1-(.alpha.-alkoxybenzyl)benzotriazoles to enol ethers. New routes to 1,3-diethers

  摘要：

  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.

  DOI：

  10.1021/jo00044a030

文献信息

• Electrochemical Three‐Component Reaction to Construct <i>N</i>‐(<i>α</i>‐alkoxyalkyl)benzotriazoles
  作者：Han‐Fu Liu、Yang Li、Guo‐Ao Wang、Kai‐Wei Chen、Hai‐Tao Tang、Ying‐Ming Pan、Mu‐Xue He、Ke‐Di Yang、Yong‐Lin Huang

  DOI：10.1002/adsc.202300593

  日期：2023.11.7

  N-(α-alkoxyalkyl)benzotriazoles are of great importance for biochemical and antitumor activity. A feasible protocol has been developed for the synthesis of N-(α-alkoxyalkyl)benzotriazoles using azoles, aldehydes and alcohols as substrates under electrochemical conditions. The reaction is carried out under acid catalyst- and oxidant-free conditions, so that a variety of synthetically useful nitrogen

  N- ( α-烷氧基烷基)苯并三唑对于生化和抗肿瘤活性具有重要意义。开发了一种在电化学条件下以唑类、醛类和醇类为底物合成N- ( α-烷氧基烷基)苯并三唑的可行方案。该反应在无酸催化剂和氧化剂的条件下进行，可以获得多种合成有用的氮杂环衍生物。更有意义的是，采用克级合成方法来证明这种转化的放大适用性。
• 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.
• Synthesis of Acyltrifluoroborates
  作者：Aaron M. Dumas、Jeffrey W. Bode

  DOI：10.1021/ol300668m

  日期：2012.4.20

  Acylboranes are among the most elusive boron-containing organic functional groups, a fact that has impeded development of new reactions employing them as substrates. A new synthesis of acyltrifluoroborates from benzotriazole (Bt)-based N,O-acetals has been developed. Two other routes provide acyltrifluoroborates containing alcohols, aldehydes, and carbamates. The ketone-like reactivity of the acyltrifluoroborate functional group is demonstrated, and the first X-ray structure of an acyltrifluoroborate is reported.
• Preparation of 1,2- and 1,4-diols via selective cleavage of C-benzotriazole bonds in reductive lithiations of N-(α-alkoxy-benzyl- and -allyl-)benzotriazoles
  作者：Alan R. katritzky、Weiliang Bao、Ming Qi、Clara N. Fali、Indra Prakash

  DOI：10.1016/s0040-4039(98)01390-2

  日期：1998.9

  Selective cleavage of C-benzotriazole bonds in the presence of C-O bonds is reported for the reductive lithiation of N-(alpha-alkoxybenzyl)benzotriazoles and N-(alpha-alkoxyallyl)benzotriazoles in a one-step or two-step process. Trapping of the intermediates with carbonyl compounds gave unsymmetrically protected 1,2 or 1,4-diols in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of β-Alkoxy Ketones and α‘-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons
  作者：Alan R. Katritzky、Daming Feng、Ming Qi

  DOI：10.1021/jo971630v

  日期：1998.3.1

  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.