(2S*,3S*)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene | 857802-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S*,3S*)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: (2SR,3SR)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene；1-[(2S,3S)-3-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]ethanone
• CAS: 857802-75-6
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: OCIQJFACUKFCTF-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[(trimethylsilyl)methyl]benzyl alcohol 在 potassium fluoride 、 18-冠醚-6 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 43.0h， 生成 (2S*,3S*)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  2-[(Trimethylsilyl)methyl]benzyl Methanesulfonates: Useful Precursors for the Generation of o-Quinodimethanes

  摘要：

  2-[(Trimethylsilyl)methyl]benzyl methanesulfonates react with potassium fluoride in the presence of a catalytic amount of 18-crown-6 at room temperature to give o-quinodimethanes, which are trapped with electron-deficient olefins to afford [4+2] cycloadducts in good yields.

  DOI：

  10.1055/s-0033-1341238

文献信息

• Potassium Fluoride-induced 1,4-Elimination of<i>o</i>-[(Trimethylsilyl)methyl]benzyl Acetates: A Versatile Generation of<i>o</i>-Quinodimethanes
  作者：Ryoichi Kuwano、Takenori Shige

  DOI：10.1246/cl.2005.728

  日期：2005.5

  o-Quinodimethane interemediate was generated from o-[(trimethylsilyl)methyl]benzyl acetate with potassium fluoride. The o-quinodimethane in hand reacted with electron-deficient olefins, affording [4+2] cycloadducts, tetrahydronaphthalenes.

  o-奎诺二甲烯中间体是通过氟化钾从o-[(三甲基硅基)甲基]苄酸乙酯生成的。得到的o-奎诺二甲烯与电子缺乏的烯烃反应，生成[4+2]环加成物，即四氢萘类化合物。
• Palladium-Catalyzed Formal [4+2] Cycloaddtion of <i>o</i>-Xylylenes with Olefins
  作者：Ryoichi Kuwano、Takenori Shige

  DOI：10.1021/ja070012l

  日期：2007.4.1

  o-(Silylmethyl)benzylic carbonates reacted with various conjugated olefins in the presence of the palladium catalyst, which was generated in situ from Pd(eta(3)-C3H5)Cp and 1,2-bis(diphenylphosphino)ethane (DPPE). The reaction provided 2- and/or 3-substituted tetralins in good yield. The catalytic reaction described here is equivalent to the [4+2] cycloaddition of o-xylylenes with dienophiles.
• 2-[(Trimethylsilyl)methyl]benzyl Methanesulfonates: Useful Precursors for the Generation of o-Quinodimethanes
  作者：Hiroshi Sano、Hidenori Shirakawa

  DOI：10.1055/s-0033-1341238

  日期：——

  2-[(Trimethylsilyl)methyl]benzyl methanesulfonates react with potassium fluoride in the presence of a catalytic amount of 18-crown-6 at room temperature to give o-quinodimethanes, which are trapped with electron-deficient olefins to afford [4+2] cycloadducts in good yields.