N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide | 352708-79-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide
• 英文别名: 3-[tert-butyl(diphenyl)silyl]-N,N-dimethylpropanamide
• CAS: 352708-79-3
• 化学式: C₂₁H₂₉NOSi
• 分子量: 339.553
• InChiKey: OZDLAODOOCOYJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(tert-Butyl-hydroxy-phenyl-silanyl)-N,N-dimethyl-propionamide
  参考文献：
  名称：

  Studies in silanol synthesis: internal nucleophiles and steric hindrance

  摘要：

  As a model system for the synthesis of complex silanediols, N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide was prepared and treated with triflic acid, resulting in the removal of one phenyl group and yielding a silanol. Even with a large excess of triflic acid, only a single phenyl group could be removed. This contrasts with a diphenylsilyl group flanked by a pair of amides, for which both phenyl groups are rapidly cleaved. A combination of steric hindrance by the tert-butyl group and lack of a second internal nucleophile appears to limit triflic acid-mediated phenyl hydrolysis from the silicon. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00576-7
• 作为产物：
  描述：

  3-(tert-butyldiphenylsilyl)propene 在 sodium hydroxide 、 potassium permanganate 、 四丙基高钌酸铵 、 硼烷 、 双氧水 、 三甲基乙酰氯 、 三乙胺 作用下， 生成 N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide
  参考文献：
  名称：

  Studies in silanol synthesis: internal nucleophiles and steric hindrance

  摘要：

  As a model system for the synthesis of complex silanediols, N,N-dimethyl 3-(tert-butyldiphenylsilyl)propionamide was prepared and treated with triflic acid, resulting in the removal of one phenyl group and yielding a silanol. Even with a large excess of triflic acid, only a single phenyl group could be removed. This contrasts with a diphenylsilyl group flanked by a pair of amides, for which both phenyl groups are rapidly cleaved. A combination of steric hindrance by the tert-butyl group and lack of a second internal nucleophile appears to limit triflic acid-mediated phenyl hydrolysis from the silicon. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00576-7