1-[(E)-3,3,3-trideuterio-2-methylprop-1-enyl]-3-(trifluoromethyl)benzene | 509095-93-6

• 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: 1-[(E)-3,3,3-trideuterio-2-methylprop-1-enyl]-3-(trifluoromethyl)benzene
• CAS: 509095-93-6
• 化学式: C₁₁H₁₁F₃
• 分子量: 203.18
• InChiKey: YJEMFCXAXFAFBS-ZJHRAVIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(E)-3,3,3-trideuterio-2-methylprop-1-enyl]-3-(trifluoromethyl)benzene 在 thionin-supported Na-Y zeolite 、 氧气 作用下， 以 正己烷 为溶剂， 反应 0.08h， 生成 1-(3,3-Dideuterio-1-deuterioperoxy-2-methylprop-2-enyl)-3-(trifluoromethyl)benzene 、 1-[1-Hydroperoxy-2-(trideuteriomethyl)prop-2-enyl]-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  Ene Hydroperoxidation of Isobutenylarenes within Dye-Exchanged Zeolite Na−Y:  Control of Site Selectivity by Cation−Arene Interactions

  摘要：

  The site selectivity in the singlet oxygen ene reaction of several deuterium-labeled isobutenylarenes depends on the position and the electronic nature of the aryl substitutents. For example, 1-(4-trifluoromethylphenyl)-2-methylpropene gives 82% twin selectivity whereas the isomeric 1-(2-trifluoromethylphenyl)-2-methylpropene gives 68% twix selectivity. If photooxygenation of these CF3-substituted compounds is carried out in solution, the opposite selectivity trends are found. On the basis of DFT calculations, these results are rationalized in terms of oxygen-cation and cation-arene interactions.

  DOI：

  10.1021/jo020599g
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 在 N-氯代丁二酰亚胺 、 lithium aluminium deuteride 、 二甲基硫 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 1-[(E)-3,3,3-trideuterio-2-methylprop-1-enyl]-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  Ene Hydroperoxidation of Isobutenylarenes within Dye-Exchanged Zeolite Na−Y:  Control of Site Selectivity by Cation−Arene Interactions

  摘要：

  The site selectivity in the singlet oxygen ene reaction of several deuterium-labeled isobutenylarenes depends on the position and the electronic nature of the aryl substitutents. For example, 1-(4-trifluoromethylphenyl)-2-methylpropene gives 82% twin selectivity whereas the isomeric 1-(2-trifluoromethylphenyl)-2-methylpropene gives 68% twix selectivity. If photooxygenation of these CF3-substituted compounds is carried out in solution, the opposite selectivity trends are found. On the basis of DFT calculations, these results are rationalized in terms of oxygen-cation and cation-arene interactions.

  DOI：

  10.1021/jo020599g

文献信息

• Ene Hydroperoxidation of Isobutenylarenes within Dye-Exchanged Zeolite Na−Y:  Control of Site Selectivity by Cation−Arene Interactions
  作者：Manolis Stratakis、Constantinos Rabalakos、Giannis Mpourmpakis、George E. Froudakis

  DOI：10.1021/jo020599g

  日期：2003.4.1

  The site selectivity in the singlet oxygen ene reaction of several deuterium-labeled isobutenylarenes depends on the position and the electronic nature of the aryl substitutents. For example, 1-(4-trifluoromethylphenyl)-2-methylpropene gives 82% twin selectivity whereas the isomeric 1-(2-trifluoromethylphenyl)-2-methylpropene gives 68% twix selectivity. If photooxygenation of these CF3-substituted compounds is carried out in solution, the opposite selectivity trends are found. On the basis of DFT calculations, these results are rationalized in terms of oxygen-cation and cation-arene interactions.