6-[3-(3,4-Dimethoxy-phenyl)-2-trimethylsilanyloxy-propyl]-4,5-dihydro-2H-pyridazin-3-one | 152560-85-5

• 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: 6-[3-(3,4-Dimethoxy-phenyl)-2-trimethylsilanyloxy-propyl]-4,5-dihydro-2H-pyridazin-3-one
• 英文别名: 3-[3-(3,4-dimethoxyphenyl)-2-trimethylsilyloxypropyl]-4,5-dihydro-1H-pyridazin-6-one
• CAS: 152560-85-5
• 化学式: C₁₈H₂₈N₂O₄Si
• 分子量: 364.517
• InChiKey: ATDQEJAWEHVXDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[3-(3,4-Dimethoxy-phenyl)-2-trimethylsilanyloxy-propyl]-4,5-dihydro-2H-pyridazin-3-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 以60%的产率得到3-(6,7-Dimethoxy-naphthalen-1-yl)-propionic acid hydrazide
  参考文献：
  名称：

  An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2-pyridazinones into 3-(1-naphthyl)propionic acid esters

  摘要：

  Treatment of 6-(3-phenyl-2-hydroxypropyl)4,5-dihydro-3(2H)-pyridazinones 6a-c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a-c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggests, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.

  DOI：

  10.1016/s0040-4039(00)79226-4
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 6-[3-(3,4-Dimethoxy-phenyl)-2-hydroxy-propyl]-4,5-dihydro-2H-pyridazin-3-one 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以82%的产率得到6-[3-(3,4-Dimethoxy-phenyl)-2-trimethylsilanyloxy-propyl]-4,5-dihydro-2H-pyridazin-3-one
  参考文献：
  名称：

  An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2-pyridazinones into 3-(1-naphthyl)propionic acid esters

  摘要：

  Treatment of 6-(3-phenyl-2-hydroxypropyl)4,5-dihydro-3(2H)-pyridazinones 6a-c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a-c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggests, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.

  DOI：

  10.1016/s0040-4039(00)79226-4

文献信息

• An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2-pyridazinones into 3-(1-naphthyl)propionic acid esters
  作者：Pier Giovanni Baraldi、Stefano Manfredini、Daniele Simoni、Glampiero Spalluto

  DOI：10.1016/s0040-4039(00)79226-4

  日期：1993.6

  Treatment of 6-(3-phenyl-2-hydroxypropyl)4,5-dihydro-3(2H)-pyridazinones 6a-c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a-c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggests, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.