2-[[3,5-dimethoxy-4-(3-methyl-2-butenyl)]phenyl]-6-(tert-butyldimethylsilanyloxy)benzofuran | 218444-39-4

• 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: 2-[[3,5-dimethoxy-4-(3-methyl-2-butenyl)]phenyl]-6-(tert-butyldimethylsilanyloxy)benzofuran
• 英文别名: Tert-butyl-[[2-[3,5-dimethoxy-4-(3-methylbut-2-enyl)phenyl]-1-benzofuran-6-yl]oxy]-dimethylsilane
• CAS: 218444-39-4
• 化学式: C₂₇H₃₆O₄Si
• 分子量: 452.666
• InChiKey: MLOKFUXAUVQFFO-UHFFFAOYSA-N

物化性质

• 沸点：
  498.1±45.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[3,5-dimethoxy-4-(3-methyl-2-butenyl)]phenyl]-6-(tert-butyldimethylsilanyloxy)benzofuran 在 正丁基锂 、 二苯基膦 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.0h， 以57%的产率得到桑辛素 C; 5-(6-羟基-2-苯并呋喃基)-2-(3-甲基-2-丁烯基)-1,3-苯二醇
  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
• 作为产物：
  描述：

  2-(3,5-二甲氧基苯基)苯并呋喃-6-醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-[[3,5-dimethoxy-4-(3-methyl-2-butenyl)]phenyl]-6-(tert-butyldimethylsilanyloxy)benzofuran
  参考文献：
  名称：

  McAllister, Graeme D.; Hartley, Richard C.; Dawson, Michael J., Journal of the Chemical Society. Perkin transactions I, 1998, # 20, p. 3453 - 3457

  摘要：

  DOI：

文献信息

• McAllister, Graeme D.; Hartley, Richard C.; Dawson, Michael J., Journal of the Chemical Society. Perkin transactions I, 1998, # 20, p. 3453 - 3457
  作者：McAllister, Graeme D.、Hartley, Richard C.、Dawson, Michael J.、Knaggs, Andrew R.

  DOI：——

  日期：——
• 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.