(±)-1-acetyl-7-(3’,4’-dihydroxy-3’-methylbutan-1’-yl)-4,6-dimethyl-5-methoxybenzotriazole | 1170950-12-5

• 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-acetyl-7-(3’,4’-dihydroxy-3’-methylbutan-1’-yl)-4,6-dimethyl-5-methoxybenzotriazole
• 英文别名: 1-[7-(3,4-Dihydroxy-3-methylbutyl)-5-methoxy-4,6-dimethylbenzotriazol-1-yl]ethanone；1-[7-(3,4-dihydroxy-3-methylbutyl)-5-methoxy-4,6-dimethylbenzotriazol-1-yl]ethanone
• CAS: 1170950-12-5
• 化学式: C₁₆H₂₃N₃O₄
• 分子量: 321.376
• InChiKey: KQNBSLKINHDNHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (±)-1-acetyl-7-(3’,4’-dihydroxy-3’-methylbutan-1’-yl)-4,6-dimethyl-5-methoxybenzotriazole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 potassium carbonate 、 二乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 48.0h， 生成 (6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol
  参考文献：
  名称：

  A New Tactic for Tocopherol Synthesis Using Intramolecular Benzyne Trapping by an Alcohol

  摘要：

  A formal total synthesis of (S)-alpha-tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.This paper is dedicated to Professor Lutz Tietze on his 75th birthday, with all best wishes.

  DOI：

  10.3987/com-15-s(t)52
• 作为产物：
  描述：

  2,6-二甲基大茴香醚 在 盐酸 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 20% palladium hydroxide-activated charcoal 、 氢气 、 硝酸 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 环己烷 、 水 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 107.67h， 生成 (±)-1-acetyl-7-(3’,4’-dihydroxy-3’-methylbutan-1’-yl)-4,6-dimethyl-5-methoxybenzotriazole
  参考文献：
  名称：

  A New Tactic for Tocopherol Synthesis Using Intramolecular Benzyne Trapping by an Alcohol

  摘要：

  A formal total synthesis of (S)-alpha-tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.This paper is dedicated to Professor Lutz Tietze on his 75th birthday, with all best wishes.

  DOI：

  10.3987/com-15-s(t)52

文献信息

• A synthesis of α-tocopherol featuring benzyne trapping by an alcohol
  作者：David W. Knight、Xu Qing

  DOI：10.1016/j.tetlet.2009.03.022

  日期：2009.7

  A formal total synthesis of alpha-tocopherol, the main component of Vitamin E, has been achieved in which a central step is the intramolecular trapping of a highly substituted benzyne by an alcohol group to establish the pyran ring. (C) 2009 Elsevier Ltd. All right reserved.
• A New Tactic for Tocopherol Synthesis Using Intramolecular Benzyne Trapping by an Alcohol
  作者：David W. Knight、Qing Xu

  DOI：10.3987/com-15-s(t)52

  日期：——

  A formal total synthesis of (S)-alpha-tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.This paper is dedicated to Professor Lutz Tietze on his 75th birthday, with all best wishes.