bis[(2S)-1-methoxy-1-oxopropan-2-yl] 9-(1,3-benzodioxol-5-yl)-6-hydroxybenzo[g][1,3]benzodioxole-7,8-dicarboxylate | 175883-66-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: bis[(2S)-1-methoxy-1-oxopropan-2-yl] 9-(1,3-benzodioxol-5-yl)-6-hydroxybenzo[g][1,3]benzodioxole-7,8-dicarboxylate
• CAS: 175883-66-6
• 化学式: C₂₈H₂₄O₁₃
• 分子量: 568.491
• InChiKey: WMVZWXZIEYVGTM-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  5-(1,3-二氧戊环-2-基)苯并-1,3-二氧杂环戊烯 在 正丁基锂 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.92h， 生成 bis[(2S)-1-methoxy-1-oxopropan-2-yl] 9-(1,3-benzodioxol-5-yl)-6-hydroxybenzo[g][1,3]benzodioxole-7,8-dicarboxylate
  参考文献：
  名称：

  Hindered Rotation in Arylnaphthalene Lignans

  摘要：

  Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

  DOI：

  10.1021/jo952048e

文献信息

• Hindered Rotation in Arylnaphthalene Lignans
  作者：James L. Charlton、Curtis J. Oleschuk、Gaik-Lean Chee

  DOI：10.1021/jo952048e

  日期：1996.1.1

  Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.