1-phenyl-4-trifluoromethyl-3,4-dihydro-1H-2-benzopyran | 1145778-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-phenyl-4-trifluoromethyl-3,4-dihydro-1H-2-benzopyran
• 英文别名: 1-Phenyl-4-(trifluoromethyl)-3,4-dihydro-1H-2-benzopyran；1-phenyl-4-(trifluoromethyl)-3,4-dihydro-1H-isochromene
• CAS: 1145778-14-8
• 化学式: C₁₆H₁₃F₃O
• 分子量: 278.274
• InChiKey: QYKUYUSUSZBKEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenyl[2-(3,3,3-trifluoroprop-1-en-2-yl)phenyl]methanol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 24.0h， 以86%的产率得到1-phenyl-4-trifluoromethyl-3,4-dihydro-1H-2-benzopyran
  参考文献：
  名称：

  Synthesis of Isochromanes and Isothiochromanes Bearing Fluorinated One-Carbon Units via Intramolecular Cyclizations of ortho-Substituted α-(Trifluoromethyl)styrenes

  摘要：

  alpha-(Trifluoromethyl)styrenes bearing a nucleophilic oxygen or sulfur atom tethered by a methylene or methyne unit at the ortho carbon were prepared by the coupling reaction of 2-bromo-3,3,3-trifluoropropene with aryl iodides via (3,3,3-trifluoroprop-1-en-2-yl) boronic acid. The styrenes thus obtained readily undergo an intramolecular nucleophilic addition or substitution (S(N)2'-type) of the oxygen and sulfur under basic conditions, leading to 4-trifluoromethyl- or 4-difluoromethylene-substituted isochromanes and isothiochromanes, respectively.

  DOI：

  10.3987/com-08-s(f)114

文献信息

• Synthesis of Isochromanes and Isothiochromanes Bearing Fluorinated One-Carbon Units via Intramolecular Cyclizations of ortho-Substituted α-(Trifluoromethyl)styrenes
  作者：Junji Ichikawa、Masahiro Ikeda、Masahiro Hattori

  DOI：10.3987/com-08-s(f)114

  日期：——

  alpha-(Trifluoromethyl)styrenes bearing a nucleophilic oxygen or sulfur atom tethered by a methylene or methyne unit at the ortho carbon were prepared by the coupling reaction of 2-bromo-3,3,3-trifluoropropene with aryl iodides via (3,3,3-trifluoroprop-1-en-2-yl) boronic acid. The styrenes thus obtained readily undergo an intramolecular nucleophilic addition or substitution (S(N)2'-type) of the oxygen and sulfur under basic conditions, leading to 4-trifluoromethyl- or 4-difluoromethylene-substituted isochromanes and isothiochromanes, respectively.