2,2-di(1H-1,2,3-benzotriazol-1-yl)-1,1-diphenyl-1-ethanol | 495401-40-6

• 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: 2,2-di(1H-1,2,3-benzotriazol-1-yl)-1,1-diphenyl-1-ethanol
• 英文别名: 2,2-di(1,2,3-benzotriazol-1-yl)-1,1-diphenyl-1-ethanol；2,2-Bis(benzotriazol-1-yl)-1,1-diphenylethanol
• CAS: 495401-40-6
• 化学式: C₂₆H₂₀N₆O
• 分子量: 432.484
• InChiKey: DUDCNUWKAZAQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-di(1H-1,2,3-benzotriazol-1-yl)-1,1-diphenyl-1-ethanol 在 zinc dibromide 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 64.0h， 以20%的产率得到1-[1-(1,2,3-benzotriazol-1-yl)-2,2-diphenylvinyl]-1,2,3-benzotriazole
  参考文献：
  名称：

  General and Efficient Insertion of Carbons Carrying Benzotriazole

  摘要：

  Anions formed from the lithiation of 1-(1-benzotriazolylalkyl)benzotriazoles (1, 6) and 1-(1-methylthioalkyl)benzotriazoles (10 and 10a) with n-BuLi underwent additions to cyclic and acyclic ketones giving intermediates 3a-f, 7b-f, and 11b-d, respectively, in excellent yields. Thermal rearrangements of intermediates 3a,b,d-f and 7b-d,f in the presence of zinc bromide provided one-carbon chain-extended or ring-expanded cc-benzotriazolyl ketones 4a,b,d-f and 8b-d,f in moderate yields with excellent regioselectivity. By contrast, intermediates 11b-d on treatment with zinc bromide loose a molecule of benzotriazole followed by intramolecular cyclization of the resulting intermediates 12b-d to provide the 2,3- and 1,2,3-substituted indenes 13b-d in good yields.

  DOI：

  10.1021/jo035098p
• 作为产物：
  描述：

  二苯甲酮 、 1-(苯并三唑-1-基甲基)苯并三唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以85%的产率得到2,2-di(1H-1,2,3-benzotriazol-1-yl)-1,1-diphenyl-1-ethanol
  参考文献：
  名称：

  General and Efficient Insertion of Carbons Carrying Benzotriazole

  摘要：

  Anions formed from the lithiation of 1-(1-benzotriazolylalkyl)benzotriazoles (1, 6) and 1-(1-methylthioalkyl)benzotriazoles (10 and 10a) with n-BuLi underwent additions to cyclic and acyclic ketones giving intermediates 3a-f, 7b-f, and 11b-d, respectively, in excellent yields. Thermal rearrangements of intermediates 3a,b,d-f and 7b-d,f in the presence of zinc bromide provided one-carbon chain-extended or ring-expanded cc-benzotriazolyl ketones 4a,b,d-f and 8b-d,f in moderate yields with excellent regioselectivity. By contrast, intermediates 11b-d on treatment with zinc bromide loose a molecule of benzotriazole followed by intramolecular cyclization of the resulting intermediates 12b-d to provide the 2,3- and 1,2,3-substituted indenes 13b-d in good yields.

  DOI：

  10.1021/jo035098p

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.