(S)-1-(2-methoxy-phenyl)-4-oxiranylmethyl-piperazine | 1621070-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-1-(2-methoxy-phenyl)-4-oxiranylmethyl-piperazine
• 英文别名: 1-(2-methoxyphenyl)-4-[[(2S)-oxiran-2-yl]methyl]piperazine
• CAS: 1621070-08-3
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: OCXUZXFYKMTQNS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  萘酚 、 (S)-1-(2-methoxy-phenyl)-4-oxiranylmethyl-piperazine 在 四丁基氟化铵 、 silver nitrate 作用下， 以 异丙醇 为溶剂， 反应 13.0h， 以48%的产率得到(S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol
  参考文献：
  名称：

  Silver nanoparticle-catalysed phenolysis of epoxides under neutral conditions: Scope and limitations of metal nanoparticles and applications towards drug synthesis

  摘要：

  Chemo- and regio-selective epoxide phenolysis is reported for the first time under neutral condition catalysed by silver nanoparticles. Other metal nanoparticles (e.g., Au, Pd, Cu, In, and Ru) are less effective. The choice of solvent is critical with 2-propanol being the best followed by DEF. Amongst various stabilisers used (surfactants, PEGs, tetra-allcylammonium halides) the tetra-alkylammonium halides are found to be the most effective (TBAF > TBAB > TBACl > TBAI). The role of the silver nanoparticles is envisaged as synchronous mode epoxide-phenol dual activation via a cooperative network of coordination, anion-it interaction, and hydrogen bond. The silver nanoparticles are recovered and reused for five consecutive times. The reaction has been used for the synthesis of propranolol and naftopidil as a few representative cardiovascular drugs. (C) 2014 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcata.2014.05.011
• 作为产物：
  描述：

  左旋环氧氯丙烷 、 1-(2-甲氧苯基)哌嗪 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以70%的产率得到(S)-1-(2-methoxy-phenyl)-4-oxiranylmethyl-piperazine
  参考文献：
  名称：

  Silver nanoparticle-catalysed phenolysis of epoxides under neutral conditions: Scope and limitations of metal nanoparticles and applications towards drug synthesis

  摘要：

  Chemo- and regio-selective epoxide phenolysis is reported for the first time under neutral condition catalysed by silver nanoparticles. Other metal nanoparticles (e.g., Au, Pd, Cu, In, and Ru) are less effective. The choice of solvent is critical with 2-propanol being the best followed by DEF. Amongst various stabilisers used (surfactants, PEGs, tetra-allcylammonium halides) the tetra-alkylammonium halides are found to be the most effective (TBAF > TBAB > TBACl > TBAI). The role of the silver nanoparticles is envisaged as synchronous mode epoxide-phenol dual activation via a cooperative network of coordination, anion-it interaction, and hydrogen bond. The silver nanoparticles are recovered and reused for five consecutive times. The reaction has been used for the synthesis of propranolol and naftopidil as a few representative cardiovascular drugs. (C) 2014 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcata.2014.05.011