(R)-(-)-2-(2-methoxyphenyl)-1-phenylethanol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-(-)-2-(2-methoxyphenyl)-1-phenylethanol
• 英文别名: (R)-2-(2-methoxyphenyl)-1-phenylethan-1-ol；(1R)-2-(2-methoxyphenyl)-1-phenylethanol
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: SGDZOSZXAQKDQA-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-环氧苯乙烷 、 苯甲醚 在 正丁基锂 、 四甲基乙二胺 、 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以79%的产率得到(R)-(-)-2-(2-methoxyphenyl)-1-phenylethanol
  参考文献：
  名称：

  Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3·OEt2

  摘要：

  It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3 center dot OEt2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of (BuLi)-Bu-n and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with (BuLi)-Bu-n in THE as usual. Surprisingly, the availability of THE and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.116

文献信息

• Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3·OEt2
  作者：Erkan Ertürk、Mustafa A. Tezeren、Taner Atalar、Tahir Tilki

  DOI：10.1016/j.tet.2012.05.116

  日期：2012.8

  It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3 center dot OEt2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of (BuLi)-Bu-n and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with (BuLi)-Bu-n in THE as usual. Surprisingly, the availability of THE and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides. (C) 2012 Elsevier Ltd. All rights reserved.