(1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol | 853786-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol
• CAS: 853786-31-9
• 化学式: C₁₃H₂₀O₇
• 分子量: 288.298
• InChiKey: LGIDSFYPUROGSL-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol 在 palladium on activated charcoal 吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 36.0h， 生成 (1'R,2'S)-4-hydroxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035
• 作为产物：
  描述：

  ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate 在 AD-mix-α 、 甲基磺酰胺 、 二异丁基氢化铝 作用下， 以 正己烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol
  参考文献：
  名称：

  An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

  摘要：

  The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-beta to give triol (1R,2R)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These Studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2' and C-3'. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.035