2,4-Ditert-butyl-6-hex-1-ynylphenol | 177721-02-7

• 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: 2,4-Ditert-butyl-6-hex-1-ynylphenol
• CAS: 177721-02-7
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: NLRLHDPEYVLAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  叔丁基过氧化氢 、 2,4-Ditert-butyl-6-hex-1-ynylphenol 在 salcomine 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到2,4-Ditert-butyl-4-tert-butylperoxy-6-hex-1-ynylcyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Co(salen)-Catalyzed tert-Butyl Hydroperoxide Oxidation of tert-Butylphenols Bearing an Unsaturated Side Chain

  摘要：

  Co(salen)-catalyzed oxidation of 2,4- and 2,6-di-tert-butylphenols bearing an unsaturated side chain, with tert-butyl hydroperoxide (TBHP) in CH2Cl2 at rt, results predominantly in the formation of tert-butylperoxylated products. The position of tert-butylperoxylation depends on the nature of the unsaturated side chain: predominantly the ortho position for 4-alkynyl-2,6-di-tert-butylphenols, the side chain for 4-alkenyl-2,6-di-tert-butylphenols, and the para position for 4-cyano- or 4-(1-methoxyimino)alkyl-2,6-di-tert-butylphenols as well as 2-alkynyl-, 2-alkenyl-, and 2-cyano-4,6-di-tert-butylphenols. The ortho tert-butylperoxylated products arise mainly from initially formed para tert-butylperoxylated products, by migration of the tert-butylperoxy group.

  DOI：

  10.1021/jo950944k
• 作为产物：
  描述：

  3,5-二叔丁基邻苯醌 在 盐酸 、 乙基溴化镁 、 锌 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2,4-Ditert-butyl-6-hex-1-ynylphenol
  参考文献：
  名称：

  Co(salen)-Catalyzed tert-Butyl Hydroperoxide Oxidation of tert-Butylphenols Bearing an Unsaturated Side Chain

  摘要：

  Co(salen)-catalyzed oxidation of 2,4- and 2,6-di-tert-butylphenols bearing an unsaturated side chain, with tert-butyl hydroperoxide (TBHP) in CH2Cl2 at rt, results predominantly in the formation of tert-butylperoxylated products. The position of tert-butylperoxylation depends on the nature of the unsaturated side chain: predominantly the ortho position for 4-alkynyl-2,6-di-tert-butylphenols, the side chain for 4-alkenyl-2,6-di-tert-butylphenols, and the para position for 4-cyano- or 4-(1-methoxyimino)alkyl-2,6-di-tert-butylphenols as well as 2-alkynyl-, 2-alkenyl-, and 2-cyano-4,6-di-tert-butylphenols. The ortho tert-butylperoxylated products arise mainly from initially formed para tert-butylperoxylated products, by migration of the tert-butylperoxy group.

  DOI：

  10.1021/jo950944k

文献信息

• An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo202207s

  日期：2012.1.6

  A copper-catalyzed annulative amination approach to 3-aminobenzofurans and -indoles from o-alkynylphenols and -anilines has been developed. The Cu-based catalysis is based on an umpolung, electrophilic amination with O-benzoyl hydroxylamines and enables the mild and convergent synthesis of various 3-aminobenzoheteroles of biological and pharmaceutical interest. Some mechanistic investigations and an application of this protocol to construction of more complex tricyclic framework are also described.
• Copper-Catalyzed Annulative Amination of <i>ortho</i>-Alkynylphenols with Hydroxylamines: Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy
  作者：Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol200651r

  日期：2011.5.6

  A room temperature copper-catalyzed annulative amination of ortho-alkynylphenols with electrophilic amination reagents, O-acylated hydroxylamines, proceeds efficiently to provide the corresponding 3-aminobenzofurans of biological and pharmaceutical interest.

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