1-(1-oxaspiro[2.5]oct-2-yl)-1H-1,2,3-benzotriazole | 495401-35-9

• 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: 1-(1-oxaspiro[2.5]oct-2-yl)-1H-1,2,3-benzotriazole
• 英文别名: 1-(1-Oxaspiro[2.5]octan-2-yl)benzotriazole
• CAS: 495401-35-9
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: IESAVBANGXBPNC-UHFFFAOYSA-N

物化性质

• 沸点：
  425.8±38.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 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-(1-oxaspiro[2.5]oct-2-yl)-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 1-(1-hydroxycyclohexyl)-2-phenyl-1,2-ethanedione
  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：

  1-(氯甲基)-1H-苯并三唑 、 环己酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以70%的产率得到1-(1-oxaspiro[2.5]oct-2-yl)-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.