2-(4-methylbenzenesulfonyl)-3-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydroisoquinoline | 1182624-49-2

• 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-methylbenzenesulfonyl)-3-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-methylphenyl)sulfonyl-3-[3-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline
• CAS: 1182624-49-2
• 化学式: C₂₃H₂₀F₃NO₂S
• 分子量: 431.479
• InChiKey: HPGNMQAVFNLKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-[(trimethylsilyl)methyl]benzyl methyl carbonate 、 4-methyl-N-(3-(trifluoromethyl)benzylidene)benzenesulfonamide 在 potassium fluoride 、 allyl(cyclopentadiene)palladium(II) 、 1,5-双(二苯基膦)戊烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76%的产率得到2-(4-methylbenzenesulfonyl)-3-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  [4+2] Cycloaddition of o-Xylylenes with Imines Using Palladium Catalyst

  摘要：

  The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(eta(3)-C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diets-Alder reaction of o-xylylene with imines.

  DOI：

  10.1021/ja905988e

文献信息

• [4+2] Cycloaddition of <i>o</i>-Xylylenes with Imines Using Palladium Catalyst
  作者：Satoshi Ueno、Masakazu Ohtsubo、Ryoichi Kuwano

  DOI：10.1021/ja905988e

  日期：2009.9.16

  The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(eta(3)-C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diets-Alder reaction of o-xylylene with imines.