4‐(2‐hydroxypropan‐2‐yl)‐2,6‐dimethylphenol | 55182-63-3

• 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: 4‐(2‐hydroxypropan‐2‐yl)‐2,6‐dimethylphenol
• 英文别名: 2-(3,5-dimethyl-4-hydroxyphenyl)-2-propanol；2-(4-Hydroxy-3,5-dimethylphenyl)-2-propanol；4-(2-Hydroxypropan-2-yl)-2,6-dimethylphenol
• CAS: 55182-63-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: VWIZWNKCFMODOA-UHFFFAOYSA-N

物化性质

• 沸点：
  300.8±37.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4‐(2‐hydroxypropan‐2‐yl)‐2,6‐dimethylphenol 在 甲基苯乙烯 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到1-(3,5-dimethyl-4-hydroxyphenyl)-6-hydroxy-1,3,3,5,7-pentamethyl-1,2-dihydroindene
  参考文献：
  名称：

  Formal [3+2]cycloaddition of benzylic cations with alkenes

  摘要：

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.

  DOI：

  10.1021/jo00048a029
• 作为产物：
  描述：

  甲基碘化镁 、 4-羟基-3,5-二甲基苯甲酸甲酯 生成 4‐(2‐hydroxypropan‐2‐yl)‐2,6‐dimethylphenol
  参考文献：
  名称：

  Pospisek,J. et al., Collection of Czechoslovak Chemical Communications, 1975, vol. 40, p. 142 - 148

  摘要：

  DOI：

文献信息

• Site‐selective Oxidative Dearomatization of Phenols and Naphthols into <i>ortho</i> ‐Quinols or Epoxy <i>ortho</i> ‐Quinols using Oxone as the Source of Dimethyldioxirane
  作者：María J. Cabrera‐Afonso、M. Carmen Carreño、Antonio Urbano

  DOI：10.1002/adsc.201900660

  日期：2019.10.8

  A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho‐quinols or epoxy ortho‐quinols from a site‐selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described

  报道了由Oxone和丙酮原位生成的二甲基二环氧乙烷与取代的酚和萘的新型反应性。该方法允许合成邻-quinols或环氧邻-quinols从站点选择性氧化脱芳构化过程中，随着非常温和的条件下具有良好的产率。还描述了使用该方法作为关键步骤的天然产物紫杉烯C甲醚的短暂全合成。
• Formal [3+3]- and [3+2]-cycloadditions of allylsilanes with benzylic cations
  作者：Steven R. Angle、Jim P. Boyce

  DOI：10.1016/s0040-4039(00)78246-3

  日期：1994.8

  Allylsilanes serve as three-carbon dipole equivalents for the formation of tetrahydronaphthalenes via Lewis-acid promoted formal [3+3]-cycloadditions with benzylic cations. A competing [3+2]-pathway resulted in the formation of dihydro(1H)indenes. Both quinone methides and benzylic alcohols were used as precursors to the benzylic cations.
• US4045499A
  申请人：——

  公开号：US4045499A

  公开（公告）日：1977-08-30
• Formal [3+2]cycloaddition of benzylic cations with alkenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00048a029

  日期：1992.10

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.
• Pospisek,J. et al., Collection of Czechoslovak Chemical Communications, 1975, vol. 40, p. 142 - 148
  作者：Pospisek,J. et al.

  DOI：——

  日期：——