(E)-1,1-dideuterio-2-methyl-3-(2-methylphenyl)prop-2-en-1-ol | 509095-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1,1-dideuterio-2-methyl-3-(2-methylphenyl)prop-2-en-1-ol
• CAS: 509095-77-6
• 化学式: C₁₁H₁₄O
• 分子量: 164.216
• InChiKey: WCZPRVDVXKSHLC-AYWWODINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1,1-dideuterio-2-methyl-3-(2-methylphenyl)prop-2-en-1-ol 在 N-氯代丁二酰亚胺 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(E)-3-chloro-3,3-dideuterio-2-methylprop-1-enyl]-2-methylbenzene
  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：

  (E)-3-(2-methylphenyl)-2-methyl acrylic acid methyl ester 在 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 生成 (E)-1,1-dideuterio-2-methyl-3-(2-methylphenyl)prop-2-en-1-ol
  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.