2,2,6,6-tetramethyl-1-(1-phenylpent-4-enyloxy)-piperidine | 887946-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2,2,6,6-tetramethyl-1-(1-phenylpent-4-enyloxy)-piperidine
• 英文别名: 2,2,6,6-Tetramethyl-1-(1-phenylpent-4-enoxy)piperidine；2,2,6,6-tetramethyl-1-(1-phenylpent-4-enoxy)piperidine
• CAS: 887946-51-2
• 化学式: C₂₀H₃₁NO
• 分子量: 301.472
• InChiKey: YJOZVMDHEWXEIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,6,6-tetramethyl-1-(1-phenylpent-4-enyloxy)-piperidine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 acetic acid 3-phenyl-2,3-dihydro-1H-cyclopenta[b]quinolin-9-yl methyl ester
  参考文献：
  名称：

  Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines

  摘要：

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

  DOI：

  10.1021/ol0604421
• 作为产物：
  描述：

  1-phenyl-4-penten-1-ol 在 三溴化磷 、 copper(II) bis(trifluoromethanesulfonate) 、 铜 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 乙醚 、 苯 为溶剂， 反应 21.5h， 生成 2,2,6,6-tetramethyl-1-(1-phenylpent-4-enyloxy)-piperidine
  参考文献：
  名称：

  Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines

  摘要：

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

  DOI：

  10.1021/ol0604421

文献信息

• Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines
  作者：Birgit Janza、Armido Studer

  DOI：10.1021/ol0604421

  日期：2006.4.1

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.