artoindonesianin B-1

• 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: artoindonesianin B-1
• 英文别名: 5-(6-Hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-1-enyl)benzene-1,3-diol；5-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-1-enyl)benzene-1,3-diol
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: YVWWLJFWZOKLLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Bromo-5-[tert-butyl(dimethyl)silyl]oxyphenol 在 ruthenium trichloride 、 sodium periodate 、 copper(l) iodide 、 Pd(PPh₃)₂Cl₂ 、 对甲苯磺酸 、 三乙基苯基氯化铵 、 三乙胺 、 二苯基膦酸锂 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 artoindonesianin B-1
  参考文献：
  名称：

  Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

  摘要：

  In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.093

文献信息

• Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus
  作者：Deyan Wu、Hanbing Mei、Ping Tan、Weiqiang Lu、Jin Zhu、Wei Wang、Jin Huang、Jian Li

  DOI：10.1016/j.tetlet.2015.05.093

  日期：2015.7

  In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential. (C) 2015 Elsevier Ltd. All rights reserved.