(3R,3aR,8bS)-3-((S)-1,2-dihydroxyethyl)-3a,8b-dihydroxy-6,8-dimethoxy-3,3a-dihydrofuro[3,4-b]benzofuran-1(8bH)-one | 1350802-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (3R,3aR,8bS)-3-((S)-1,2-dihydroxyethyl)-3a,8b-dihydroxy-6,8-dimethoxy-3,3a-dihydrofuro[3,4-b]benzofuran-1(8bH)-one
• 英文别名: (3R,3aR,8bS)-3-[(1S)-1,2-dihydroxyethyl]-3a,8b-dihydroxy-6,8-dimethoxy-3H-furo[3,4-b][1]benzofuran-1-one
• CAS: 1350802-52-6
• 化学式: C₁₄H₁₆O₉
• 分子量: 328.276
• InChiKey: ODJKLXASKFZZPU-AWUDHZIESA-N

物化性质

• 沸点：
  638.7±55.0 °C(Predicted)
• 密度：
  1.696±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 脱氢抗坏血酸 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(3R,3aR,8bS)-3-((S)-1,2-dihydroxyethyl)-3a,8b-dihydroxy-6,8-dimethoxy-3,3a-dihydrofuro[3,4-b]benzofuran-1(8bH)-one
  参考文献：
  名称：

  A biomimetic synthesis of (−)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues

  摘要：

  A method for appending the ascorbyl moiety onto the framework of phenolic natural products has been developed. This reaction proceeds in two steps from.-ascorbic acid and employs acetic acid catalysis. Excellent stereoselectivity is observed during C C bond formation between the phenolic compound and dehydroascorbic acid, and the process is also chemoselective for phenol derivatives bearing electron-donating substituents in each of the 1, 3, and 5 positions. Further, good regioselectivity was also observed when phenols lacking an axis of C-2 symmetry were employed. This method has led to the synthesis of (-)-ascorbyl phloroglucinol as well as the tetracyclic core of ascorbyl-modified catechin natural products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.102

文献信息

• A biomimetic synthesis of (−)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues
  作者：Sneha A. Belapure、Zachary G. Beamer、John E. Bartmess、Shawn R. Campagna

  DOI：10.1016/j.tet.2011.09.102

  日期：2011.12

  A method for appending the ascorbyl moiety onto the framework of phenolic natural products has been developed. This reaction proceeds in two steps from.-ascorbic acid and employs acetic acid catalysis. Excellent stereoselectivity is observed during C C bond formation between the phenolic compound and dehydroascorbic acid, and the process is also chemoselective for phenol derivatives bearing electron-donating substituents in each of the 1, 3, and 5 positions. Further, good regioselectivity was also observed when phenols lacking an axis of C-2 symmetry were employed. This method has led to the synthesis of (-)-ascorbyl phloroglucinol as well as the tetracyclic core of ascorbyl-modified catechin natural products. (C) 2011 Elsevier Ltd. All rights reserved.