ethyl 2-(2-bromo-4-methoxyphenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethoxy-4-oxobenzofuran-3-carboxylate | 1312466-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 2-(2-bromo-4-methoxyphenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethoxy-4-oxobenzofuran-3-carboxylate
• 英文别名: ethyl (2S,3R)-2-(2-bromo-4-methoxyphenyl)-3-hydroxy-6,6-dimethoxy-4-oxo-5,7-dihydro-2H-1-benzofuran-3-carboxylate
• CAS: 1312466-10-6
• 化学式: C₂₀H₂₃BrO₈
• 分子量: 471.302
• InChiKey: FDAPAKVJGCXERY-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甲醇 、 在 [双(三氟乙酰氧基)碘]苯 作用下， 反应 0.5h， 生成 ethyl 2-(2-bromo-4-methoxyphenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethoxy-4-oxobenzofuran-3-carboxylate 、 ethyl 2-(2-bromo-4-methoxyphenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-6,6-dimethoxy-4-oxobenzofuran-3-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.