1-(3,3-diphenyl-2-oxiranyl)-1H-1,2,3-benzotriazole | 495401-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,3-diphenyl-2-oxiranyl)-1H-1,2,3-benzotriazole
• 英文别名: 1-(3,3-Diphenyloxiran-2-yl)benzotriazole
• CAS: 495401-33-7
• 化学式: C₂₀H₁₅N₃O
• 分子量: 313.359
• InChiKey: GVPIYHMHRUMXTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  519.2±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,3-diphenyl-2-oxiranyl)-1H-1,2,3-benzotriazole 在 正丁基锂 、 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 生成 3-hydroxy-1,3,3-triphenyl-1,2-propanedione
  参考文献：
  名称：

  Lithiation of 1-Chloromethylbenzotriazole:  Generation and Elaboration of Benzotriazolyloxiranes

  摘要：

  1-Benzotriazolylchloromethyllithium generated from 1-chloromethylbenzotriazole (1) and LDA reacts with enolizable and nonenolizable ketones to give benzotriazolyloxiranes 2a-g in good yields. The oxiranyllithiums 4a-d generated from 2a-d and n-BuLi at -78 degreesC were trapped by a variety of electrophiles to give oxiranyl derivatives 5a-j in good to excellent yields. Lewis-acid-promoted nucleophilic ring opening of benzotriazolyloxiranes 2a,f,g with allyltrimethylsilane gave the corresponding 1,7-octadien-4-ols 6a-c in 68-75% yield. Hydrolysis of alpha-acylbenzotriazolyloxiranes 5g,h provided 3-hydroxy-1,2-diones 7a and 7b in 73 and 86% yield, respectively.

  DOI：

  10.1021/jo026400h
• 作为产物：
  描述：

  二苯甲酮 、 1-(氯甲基)-1H-苯并三唑 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以68%的产率得到1-(3,3-diphenyl-2-oxiranyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  Lithiation of 1-Chloromethylbenzotriazole:  Generation and Elaboration of Benzotriazolyloxiranes

  摘要：

  1-Benzotriazolylchloromethyllithium generated from 1-chloromethylbenzotriazole (1) and LDA reacts with enolizable and nonenolizable ketones to give benzotriazolyloxiranes 2a-g in good yields. The oxiranyllithiums 4a-d generated from 2a-d and n-BuLi at -78 degreesC were trapped by a variety of electrophiles to give oxiranyl derivatives 5a-j in good to excellent yields. Lewis-acid-promoted nucleophilic ring opening of benzotriazolyloxiranes 2a,f,g with allyltrimethylsilane gave the corresponding 1,7-octadien-4-ols 6a-c in 68-75% yield. Hydrolysis of alpha-acylbenzotriazolyloxiranes 5g,h provided 3-hydroxy-1,2-diones 7a and 7b in 73 and 86% yield, respectively.

  DOI：

  10.1021/jo026400h

文献信息

• Lithiation of 1-Chloromethylbenzotriazole:  Generation and Elaboration of Benzotriazolyloxiranes
  作者：Alan R. Katritzky、Kavita Manju、Peter J. Steel

  DOI：10.1021/jo026400h

  日期：2003.1.1

  1-Benzotriazolylchloromethyllithium generated from 1-chloromethylbenzotriazole (1) and LDA reacts with enolizable and nonenolizable ketones to give benzotriazolyloxiranes 2a-g in good yields. The oxiranyllithiums 4a-d generated from 2a-d and n-BuLi at -78 degreesC were trapped by a variety of electrophiles to give oxiranyl derivatives 5a-j in good to excellent yields. Lewis-acid-promoted nucleophilic ring opening of benzotriazolyloxiranes 2a,f,g with allyltrimethylsilane gave the corresponding 1,7-octadien-4-ols 6a-c in 68-75% yield. Hydrolysis of alpha-acylbenzotriazolyloxiranes 5g,h provided 3-hydroxy-1,2-diones 7a and 7b in 73 and 86% yield, respectively.