p-<(Trimethylsilyl)methyl>phenylacetic acid | 19061-70-2

• 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: p-<(Trimethylsilyl)methyl>phenylacetic acid
• 英文别名: p-Trimethylsilylmethyl-phenylessigsaeure；2-[4-(Trimethylsilylmethyl)phenyl]acetic acid
• CAS: 19061-70-2
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: HCZADAJLFMLGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  p-<(Trimethylsilyl)methyl>phenylacetic acid 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 2-[4-[(4-Cyanonaphthalen-2-yl)methyl]phenyl]acetic acid
  参考文献：
  名称：

  Methylbenzene cation radical .alpha.-fragmentation selectivities revealed in SET-photoadditions of p-xylene derivatives to 1,4-dicyanonaphthalene [SET = single electron transfer]

  摘要：

  SET-promoted photoreactions of selected p-xylene derivatives, including p-xylene (3a), p-phenylenediacetic acid (3b), p-bis[(trimethylsilyl)methyl]benzene (3c), p-[(trim ethylsilyl)methyl]toluene (3d), p-tolylacetic acid (3e), and p-[(trimethylsilyl)methyl]phenylacetic acid (3f), to 1,4-dicyanonaphthalene have been investigated. These processes lead to clean and selective formation of 1:1 adducts whose nature is controlled by alpha-heterolytic fragmentation reactions occurring at benzylic positions of arene cation radicals which serve as key reactive intermediates. The results indicate that the relative rates of cation radical fragmentations of the type ([ArCH2E].+ + B: --> ArCH2.+ BE) depend on the nature of the electrofugal group, E, in the following order: E = SiMe3 > CO2H > H. The experimental basis for these conclusions is discussed.

  DOI：

  10.1021/jo00056a029
• 作为产物：
  描述：

  (4-羟基苄基)三甲基硅烷 在 盐酸 、 magnesium 作用下， 反应 15.0h， 生成 p-<(Trimethylsilyl)methyl>phenylacetic acid
  参考文献：
  名称：

  Methylbenzene cation radical .alpha.-fragmentation selectivities revealed in SET-photoadditions of p-xylene derivatives to 1,4-dicyanonaphthalene [SET = single electron transfer]

  摘要：

  SET-promoted photoreactions of selected p-xylene derivatives, including p-xylene (3a), p-phenylenediacetic acid (3b), p-bis[(trimethylsilyl)methyl]benzene (3c), p-[(trim ethylsilyl)methyl]toluene (3d), p-tolylacetic acid (3e), and p-[(trimethylsilyl)methyl]phenylacetic acid (3f), to 1,4-dicyanonaphthalene have been investigated. These processes lead to clean and selective formation of 1:1 adducts whose nature is controlled by alpha-heterolytic fragmentation reactions occurring at benzylic positions of arene cation radicals which serve as key reactive intermediates. The results indicate that the relative rates of cation radical fragmentations of the type ([ArCH2E].+ + B: --> ArCH2.+ BE) depend on the nature of the electrofugal group, E, in the following order: E = SiMe3 > CO2H > H. The experimental basis for these conclusions is discussed.

  DOI：

  10.1021/jo00056a029

文献信息

• dAlessandro Nicola, Albini Angelo, Mariano Patrick S., J. Org. Chem., 58 (1993) N 4, S 937-942
  作者：dAlessandro Nicola, Albini Angelo, Mariano Patrick S.

  DOI：——

  日期：——
• Methylbenzene cation radical .alpha.-fragmentation selectivities revealed in SET-photoadditions of p-xylene derivatives to 1,4-dicyanonaphthalene [SET = single electron transfer]
  作者：Nicola D'Alessandro、Angelo Albini、Patrick S. Mariano

  DOI：10.1021/jo00056a029

  日期：1993.2

  SET-promoted photoreactions of selected p-xylene derivatives, including p-xylene (3a), p-phenylenediacetic acid (3b), p-bis[(trimethylsilyl)methyl]benzene (3c), p-[(trim ethylsilyl)methyl]toluene (3d), p-tolylacetic acid (3e), and p-[(trimethylsilyl)methyl]phenylacetic acid (3f), to 1,4-dicyanonaphthalene have been investigated. These processes lead to clean and selective formation of 1:1 adducts whose nature is controlled by alpha-heterolytic fragmentation reactions occurring at benzylic positions of arene cation radicals which serve as key reactive intermediates. The results indicate that the relative rates of cation radical fragmentations of the type ([ArCH2E].+ + B: --> ArCH2.+ BE) depend on the nature of the electrofugal group, E, in the following order: E = SiMe3 > CO2H > H. The experimental basis for these conclusions is discussed.