(2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid | 1489232-53-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid
• CAS: 1489232-53-2
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: WARJNTPJWCRYDW-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid 在 4-二甲氨基吡啶 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II

  摘要：

  New chalcone dimers, pauferrol B (2), and pauferrol C (3), were isolated from the stems of Caesalpinia ferrea Mart, and their structures were determined on the basis of 2D NMR spectroscopy. These new chalcone dimers showed potent inhibitory activities against human topoisomerase II and cell proliferation via the induction of apoptosis in human leukemia HL 60 cells. Absolute configurations of 2 and 3 were estimated by the comparison of CD spectra with a dihydrobenzofuran derivative 4, which was enantioselectively synthesized from 2-hydroxyphenyl acetic acid. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.028
• 作为产物：
  描述：

  2-羟基苯乙酸甲酯 在 4-二甲氨基吡啶 、 对甲苯磺酰叠氮 、 辛酸铑 、 barium hydroxide octahydrate 、 palladium 10% on activated carbon 、 水 、 氢气 、 四丁基碘化铵 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R,3R)-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid
  参考文献：
  名称：

  New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II

  摘要：

  New chalcone dimers, pauferrol B (2), and pauferrol C (3), were isolated from the stems of Caesalpinia ferrea Mart, and their structures were determined on the basis of 2D NMR spectroscopy. These new chalcone dimers showed potent inhibitory activities against human topoisomerase II and cell proliferation via the induction of apoptosis in human leukemia HL 60 cells. Absolute configurations of 2 and 3 were estimated by the comparison of CD spectra with a dihydrobenzofuran derivative 4, which was enantioselectively synthesized from 2-hydroxyphenyl acetic acid. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.028