(2S,3S,4R)-2,3-dimethoxy-4-hydroxy-3,4-dihydro-1(2H)-dibenzofuranone | 1415408-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2S,3S,4R)-2,3-dimethoxy-4-hydroxy-3,4-dihydro-1(2H)-dibenzofuranone
• 英文别名: ribisin B；Ribisin B；(2S,3S,4R)-4-hydroxy-2,3-dimethoxy-3,4-dihydro-2H-dibenzofuran-1-one
• CAS: 1415408-06-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: SWZHEXQWHYRGEY-YUTCNCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2,3-dimethoxy-4-hydroxy-3,4-dihydro-1(2H)-dibenzofuranone 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.8 mg的产率得到[(2S,3S,4R)-2,3-dimethoxy-1-oxo-3,4-dihydro-2H-dibenzofuran-4-yl] 4-bromobenzoate
  参考文献：
  名称：

  Nerve Growth Factor-Potentiating Benzofuran Derivatives from the Medicinal FungusPhellinus ribis

  摘要：

  Four new benzofuran derivatives, ribisin A (1), ribisin B (2), ribisin C (3), and ribisin D (4), were isolated from the MeOH extract of the fruiting bodies of Phellinus ribis. Their structures including their absolute configurations were determined by NMR and CD exciton chirality methods. Compounds 1-4 were found to promote neurite outgrowth in NGF-mediated PC12 cells at concentrations ranging from 1 to 30 mu M. The structure-activity relationships of these compounds are also discussed.

  DOI：

  10.1021/np300566y
• 作为产物：
  描述：

  (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 四氧化锇 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 草酰氯 、 zinc(II) acetate dihydrate 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 mineral oil 为溶剂， 反应 87.66h， 生成 (2S,3S,4R)-2,3-dimethoxy-4-hydroxy-3,4-dihydro-1(2H)-dibenzofuranone
  参考文献：
  名称：

  Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

  摘要：

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

  DOI：

  10.1021/jo500210k

文献信息

• Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties
  作者：Ping Lan、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo500210k

  日期：2014.4.4

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
• Nerve Growth Factor-Potentiating Benzofuran Derivatives from the Medicinal Fungus<i>Phellinus ribis</i>
  作者：Yuhong Liu、Miwa Kubo、Yoshiyasu Fukuyama

  DOI：10.1021/np300566y

  日期：2012.12.28

  Four new benzofuran derivatives, ribisin A (1), ribisin B (2), ribisin C (3), and ribisin D (4), were isolated from the MeOH extract of the fruiting bodies of Phellinus ribis. Their structures including their absolute configurations were determined by NMR and CD exciton chirality methods. Compounds 1-4 were found to promote neurite outgrowth in NGF-mediated PC12 cells at concentrations ranging from 1 to 30 mu M. The structure-activity relationships of these compounds are also discussed.