(2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde | 853786-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde
• 英文别名: (2R,3R)-3-[3,5-dimethoxy-4-(methoxymethoxy)phenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde
• CAS: 853786-38-6
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: VUDUPLFMIWQASR-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 乙酰氯 、 cesium fluoride 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 (1E,2'R,3'R)-5-{2'-[2',3'-dihydro-3'-(4''-hydroxy-3'',5''-dimethoxyphenyl)-2'-(hydroxymethyl)-1',4'-benzodioxin-6'-yl]ethenyl}-1,3-benzenediol
  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：

  3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 在 palladium on activated charcoal 吡啶 、 AD-mix-α 、 甲基磺酰胺 、 偶氮二甲酸二异丙酯 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 88.75h， 生成 (2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde
  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

文献信息

• An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry
  作者：Martin G. Banwell、Satish Chand、G. Paul Savage

  DOI：10.1016/j.tetasy.2005.02.035

  日期：2005.5

  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.