2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol | 1310328-62-1

• 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: 2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol
• 英文别名: 2-[2-[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]-5,6-dihydrofuro[3,2-f][1]benzofuran-6-yl]propan-2-ol
• CAS: 1310328-62-1
• 化学式: C₂₅H₃₂O₄Si
• 分子量: 424.612
• InChiKey: QGJPVKIJNONLRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol 在 吡啶 、 pyridine hydrofluoride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 {4-[6-(1-hydroxy-1-methylethyl)-5,6-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl]phenoxy}acetic acid ethyl ester
  参考文献：
  名称：

  HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues

  摘要：

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.022
• 作为产物：
  描述：

  (E)-(4-(2-bromovinyl)phenoxy)(tert-butyl)dimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正庚烷 、 乙基苯 为溶剂， 反应 22.0h， 生成 2-{6-[4-(tert-butyldimethylsilanyloxy)phenyl]-2,3-dihydrobenzo[1,2-b;5,4-b']difuran-2-yl}-propan-2-ol
  参考文献：
  名称：

  HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues

  摘要：

  The natural products moracins O and P exhibited potent in vitro inhibitory activity against hypoxia-inducible factor (HIF-1), which is a key mediator during adaptation of cancer cells to tumour hypoxia. Systematic variations of the structures of benzofuran type moracins were made and structure-activity relationship analysis showed the importance of the 2-arylbenzofuran ring and the (R)-configuration of the core scaffold. Further evaluation of the representative compound 5 showed its inhibitory effect on HIF-1 alpha protein accumulation and target gene expression under hypoxia. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.022