ethyl 3-(2-bromo-4-methoxyphenyl)-2-ethoxyoxirane-2-carboxylate | 1312466-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-(2-bromo-4-methoxyphenyl)-2-ethoxyoxirane-2-carboxylate
• 英文别名: Ethyl 3-(2-bromo-4-methoxyphenyl)-2-ethoxyoxirane-2-carboxylate
• CAS: 1312466-06-0
• 化学式: C₁₄H₁₇BrO₅
• 分子量: 345.19
• InChiKey: KROUUVCKLIKXEY-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±42.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-bromo-4-methoxyphenyl)-2-ethoxyoxirane-2-carboxylate 在 magnesium bromide 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以80%的产率得到ethyl 3-bromo-3-(2-bromo-4-methoxyphenyl)-2-oxopropanoate
  参考文献：
  名称：

  Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

  摘要：

  Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "Interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products In over 90% ee in both cases. Other key steps include an intramolecular Buohwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

  DOI：

  10.1021/ol201332u
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 正丁基锂 、 N,N,N'-三甲基乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 28.75h， 生成 ethyl 3-(2-bromo-4-methoxyphenyl)-2-ethoxyoxirane-2-carboxylate
  参考文献：
  名称：

  Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

  摘要：

  Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "Interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products In over 90% ee in both cases. Other key steps include an intramolecular Buohwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

  DOI：

  10.1021/ol201332u

文献信息

• Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol
  作者：Michael A. Calter、Na Li

  DOI：10.1021/ol201332u

  日期：2011.7.15

  Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "Interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products In over 90% ee in both cases. Other key steps include an intramolecular Buohwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.