1,1-di(1,2,3-benzotriazol-1-yl)-2-benzyl-3-phenyl-2-propanol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,1-di(1,2,3-benzotriazol-1-yl)-2-benzyl-3-phenyl-2-propanol
• 英文别名: 1,1-Bis(benzotriazol-1-yl)-2-benzyl-3-phenylpropan-2-ol
• 化学式: C₂₈H₂₄N₆O
• 分子量: 460.538
• InChiKey: QUQYYJDVZCOAQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1,1-di(1,2,3-benzotriazol-1-yl)-2-benzyl-3-phenyl-2-propanol 在 zinc dibromide 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 5.0h， 以54%的产率得到(+/-)-3-(1,2,3-benzotriazol-1-yl)-1,4-diphenyl-2-butanone
  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：

  1-(苯并三唑-1-基甲基)苯并三唑 、 二苄基甲酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以60%的产率得到1,1-di(1,2,3-benzotriazol-1-yl)-2-benzyl-3-phenyl-2-propanol
  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

• General and Efficient Insertion of Carbons Carrying Benzotriazole
  作者：Alan R. Katritzky、Sergey Bobrov、Kostyantyn Kirichenko、Yu Ji

  DOI：10.1021/jo035098p

  日期：2004.1.1

  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.