1-[3'-(1-hydroxyethyl)-5,5',6,6'-tetramethoxy-1,1'-biphenyl-3-yl]ethanone | 799775-13-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3'-(1-hydroxyethyl)-5,5',6,6'-tetramethoxy-1,1'-biphenyl-3-yl]ethanone
• 英文别名: 1-[3-[5-(1-Hydroxyethyl)-2,3-dimethoxyphenyl]-4,5-dimethoxyphenyl]ethanone；1-[3-[5-(1-hydroxyethyl)-2,3-dimethoxyphenyl]-4,5-dimethoxyphenyl]ethanone
• CAS: 799775-13-6
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: UPMNOYFYVWKUNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[3'-(1-hydroxyethyl)-5,5',6,6'-tetramethoxy-1,1'-biphenyl-3-yl]ethanone 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 (1S,1'S)-1,1'-(5,5',6,6'-tetramethoxy-1,1'-biphenyl-3,3'-diyl)diethanol 、 (1S,1'R)-1,1'-(5,5',6,6'-tetramethoxy-1,1'-biphenyl-3,3'-diyl)diethanol 、 (R)-1-[5'-((R)-1-Hydroxy-ethyl)-5,6,2',3'-tetramethoxy-biphenyl-3-yl]-ethanol
  参考文献：
  名称：

  Stereoselective oxazaborolidine–borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern

  摘要：

  The stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones with different substitution patterns on the biaryl unit was investigated, with the aim to better rationalize the factors influencing the diastereo- and enantioselectivity of the reaction for this class of compounds. The observed stereoselectivity in the reduction of diketones 6 and 7, possessing a methoxy group in the meta position with respect to the carbonyl group, is clearly dependent on the experimental conditions. The presence of an asymmetric centre in the intermediate hydroxyketone influences the global stereoselectivity in the reduction of 5 and 6, as indicated from the different selectivity ratios determined for each step of reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.066
• 作为产物：
  描述：

  1-[3-(5-乙酰基-2,3-二甲氧基-苯基)-4,5-二甲氧基-苯基]乙酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到1-[3'-(1-hydroxyethyl)-5,5',6,6'-tetramethoxy-1,1'-biphenyl-3-yl]ethanone
  参考文献：
  名称：

  Stereoselective oxazaborolidine–borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern

  摘要：

  The stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones with different substitution patterns on the biaryl unit was investigated, with the aim to better rationalize the factors influencing the diastereo- and enantioselectivity of the reaction for this class of compounds. The observed stereoselectivity in the reduction of diketones 6 and 7, possessing a methoxy group in the meta position with respect to the carbonyl group, is clearly dependent on the experimental conditions. The presence of an asymmetric centre in the intermediate hydroxyketone influences the global stereoselectivity in the reduction of 5 and 6, as indicated from the different selectivity ratios determined for each step of reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.066

文献信息

• Stereoselective oxazaborolidine–borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern
  作者：Giovanna Delogu、Maria Antonietta Dettori、Angela Patti、Sonia Pedotti

  DOI：10.1016/j.tet.2004.08.066

  日期：2004.11

  The stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones with different substitution patterns on the biaryl unit was investigated, with the aim to better rationalize the factors influencing the diastereo- and enantioselectivity of the reaction for this class of compounds. The observed stereoselectivity in the reduction of diketones 6 and 7, possessing a methoxy group in the meta position with respect to the carbonyl group, is clearly dependent on the experimental conditions. The presence of an asymmetric centre in the intermediate hydroxyketone influences the global stereoselectivity in the reduction of 5 and 6, as indicated from the different selectivity ratios determined for each step of reaction. (C) 2004 Elsevier Ltd. All rights reserved.