N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-trimethylsilylprop-1-yne | 947315-08-4

• 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: N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-trimethylsilylprop-1-yne
• 英文别名: N-[1-(4-methoxyphenyl)-3-trimethylsilylprop-2-ynyl]-4-methylbenzenesulfonamide
• CAS: 947315-08-4
• 化学式: C₂₀H₂₅NO₃SSi
• 分子量: 387.575
• InChiKey: NPKLCLYGQCGVQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-trimethylsilylprop-1-yne 在 (η⁵-cyclopentadienyl) (η⁶-naphthalene)ruthenium hexafluorophosphate 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 15.5h， 生成 N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)propanal
  参考文献：
  名称：

  Redox-Neutral Synthesis of β-Amino Aldehydes from Imines by an Alkynylation/Hydration Sequence

  摘要：

  N-Protected beta-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of the latter reaction are enhanced by the use of microwave irradiation. The possibility to carry out a one-pot Ru-catalyzed hydration/oxidation process from a terminal alkyne to a carboxylic acid was demonstrated, which provided direct access to a N-protected beta-amino acid from the corresponding terminal alkyne.

  DOI：

  10.1021/jo070745o
• 作为产物：
  描述：

  (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 、 三甲基乙炔基硅 在 Dimethylzinc 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以76%的产率得到N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-trimethylsilylprop-1-yne
  参考文献：
  名称：

  Redox-Neutral Synthesis of β-Amino Aldehydes from Imines by an Alkynylation/Hydration Sequence

  摘要：

  N-Protected beta-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of the latter reaction are enhanced by the use of microwave irradiation. The possibility to carry out a one-pot Ru-catalyzed hydration/oxidation process from a terminal alkyne to a carboxylic acid was demonstrated, which provided direct access to a N-protected beta-amino acid from the corresponding terminal alkyne.

  DOI：

  10.1021/jo070745o