p-<(trimethylsilyl)methyl>benzyl chloride | 18001-37-1

• 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>benzyl chloride
• 英文别名: <4-Chlormethyl-benzyl>-trimethylsilan；(4-Chlormethyl-benzyl)-trimethylsilan；[4-(Chloromethyl)phenyl]methyl-trimethylsilane
• CAS: 18001-37-1
• 化学式: C₁₁H₁₇ClSi
• 分子量: 212.794
• InChiKey: NOKRAZANCSYRQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  p-<(trimethylsilyl)methyl>benzyl chloride 在 盐酸 、 magnesium 作用下， 反应 15.0h， 生成 methyl 2-[4-[(1,4-dicyano-2H-naphthalen-1-yl)methyl]phenyl]acetate
  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 作用下， 反应 3.0h， 以66%的产率得到p-<(trimethylsilyl)methyl>benzyl chloride
  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

• Fluoride-induced 1,6-elimination to p-quinodimethane. A new preparative method for [2.2]paracyclophane, [2.2](2.5)furanophane and [2.2](2.5)thiophenophane
  作者：Yoshihiko Ito、Satoru Miyata、Masashi Nakatsuka、Takeo Saegusa

  DOI：10.1021/jo00318a047

  日期：1981.2
• 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：——
• ITO YOSHIHIKO; MIYATA SATORU; NAKATSUKA MASASHI; SAEGUSA TAKEO, J. ORG. CHEM., 1981, 46, NO 5, 1043-1044
  作者：ITO YOSHIHIKO、 MIYATA SATORU、 NAKATSUKA MASASHI、 SAEGUSA TAKEO

  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.