dimethyl (2R,3aR,4R,6aR,7R,9S,9aS,9bS)-2-(3-furyl)-9,9a-dihydroxy-3a,6a-dimethyldodecahydrobenzo[de]chromene-4,7-dicarboxylate | 1009091-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: dimethyl (2R,3aR,4R,6aR,7R,9S,9aS,9bS)-2-(3-furyl)-9,9a-dihydroxy-3a,6a-dimethyldodecahydrobenzo[de]chromene-4,7-dicarboxylate
• 英文别名: dimethyl (1S,3R,5R,6R,9R,10R,12S,13S)-3-(furan-3-yl)-1,12-dihydroxy-5,9-dimethyl-2-oxatricyclo[7.3.1.05,13]tridecane-6,10-dicarboxylate
• CAS: 1009091-04-6
• 化学式: C₂₂H₃₀O₈
• 分子量: 422.475
• InChiKey: VRUOCJZZVADZGZ-PQFYNLPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3aR,4R,6aR,7R,9S,9aS,9bS)-2-(3-furyl)-9,9a-dihydroxy-3a,6a-dimethyldodecahydrobenzo[de]chromene-4,7-dicarboxylate 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到dimethyl (1R,3S,4aS,5R,6R,8aR)-5-[2-(furan-3-yl)-2-hydroxyethyl]-3-hydroxy-5,8a-dimethyl-4-oxo-2,3,4a,6,7,8-hexahydro-1H-naphthalene-1,6-dicarboxylate
  参考文献：
  名称：

  Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure

  摘要：

  Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the K-Opioid receptor (KOR), were obtained in good yields. The derivatives are remarkable for their unusual and unique hemiacetal structure in the salvinorin series of compounds. The formation of the hemiacetal occurs with epimerization at C-12, thus preserving the original configuration of salvinorin A. The dimethyl ester derivative of the hemiacetal was found to have an affinity for both KOR and MOR (mu-opioid receptor). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.041
• 作为产物：
  描述：

  甲醇 、 (2R,3aR,4R,6aR,7R,9S,9aS,9bS)-2-(3-furyl)-9,9a-dihydroxy-3a,6a-dimethyldodecahydrobenzo[de]chromene-4,7-dicarboxylic acid 在 三甲基硅烷化重氮甲烷 作用下， 以 苯 为溶剂， 反应 0.5h， 以87%的产率得到dimethyl (2R,3aR,4R,6aR,7R,9S,9aS,9bS)-2-(3-furyl)-9,9a-dihydroxy-3a,6a-dimethyldodecahydrobenzo[de]chromene-4,7-dicarboxylate
  参考文献：
  名称：

  Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure

  摘要：

  Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the K-Opioid receptor (KOR), were obtained in good yields. The derivatives are remarkable for their unusual and unique hemiacetal structure in the salvinorin series of compounds. The formation of the hemiacetal occurs with epimerization at C-12, thus preserving the original configuration of salvinorin A. The dimethyl ester derivative of the hemiacetal was found to have an affinity for both KOR and MOR (mu-opioid receptor). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.041