tert-butyl 2-bromo-5-methylphenyl(((chloromethyl)dimethylsilyl)methyl)carbamate | 1370735-39-9

• 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: tert-butyl 2-bromo-5-methylphenyl(((chloromethyl)dimethylsilyl)methyl)carbamate
• CAS: 1370735-39-9
• 化学式: C₁₆H₂₅BrClNO₂Si
• 分子量: 406.823
• InChiKey: YOLGGXQZMDXVOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-bromo-5-methylphenyl(((chloromethyl)dimethylsilyl)methyl)carbamate 在 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以60%的产率得到tert-butyl 4,4,7-trimethyl-3,4-dihydrobenzo[b][1,4]azasiline-1(2H)-carboxylate
  参考文献：
  名称：

  Intramolecular Sila-Matteson Rearrangement: A General Access to Silylated Heterocycles

  摘要：

  A series of new silylated heterocycles has been efficiently prepared using an intramolecular silicon version of the Matteson rearrangement, providing two isomers of binuclear heterocycles. This method applies to a large variety of substrates, a direct relationship between the Hammett constants of the aromatic substituents and the isomer ratio being observed. Complementary experiments suggest that a common pentaorganosilicate species is involved.

  DOI：

  10.1021/ol300598s
• 作为产物：
  描述：

  双二氯甲基二甲基硅烷 、 tert-butyl (2-bromo-5-methylphenyl)carbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以68%的产率得到tert-butyl 2-bromo-5-methylphenyl(((chloromethyl)dimethylsilyl)methyl)carbamate
  参考文献：
  名称：

  Intramolecular Sila-Matteson Rearrangement: A General Access to Silylated Heterocycles

  摘要：

  A series of new silylated heterocycles has been efficiently prepared using an intramolecular silicon version of the Matteson rearrangement, providing two isomers of binuclear heterocycles. This method applies to a large variety of substrates, a direct relationship between the Hammett constants of the aromatic substituents and the isomer ratio being observed. Complementary experiments suggest that a common pentaorganosilicate species is involved.

  DOI：

  10.1021/ol300598s