3-bromo-7-methoxy-2,2-dimethylchroman-4-one | 163454-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-bromo-7-methoxy-2,2-dimethylchroman-4-one
• 英文别名: 3-bromo-7-methoxy-2,2-dimethyl-4-chromanone；3-bromo-7-methoxy-2,2-dimethyl-3H-chromen-4-one
• CAS: 163454-87-3
• 化学式: C₁₂H₁₃BrO₃
• 分子量: 285.137
• InChiKey: KGIZONQKLPXPBO-UHFFFAOYSA-N

物化性质

• 沸点：
  371.9±42.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-7-methoxy-2,2-dimethylchroman-4-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 3-Bromo-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-4-ol
  参考文献：
  名称：

  Discovery of Novel Benzopyranyl Tetracycles that Act as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand

  摘要：

  A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-kappa B transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.

  DOI：

  10.1021/jm1011269
• 作为产物：
  描述：

  7-甲氧基-2,2-二甲基苯并二氢吡喃-4-酮 在 溴 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以37%的产率得到3-bromo-7-methoxy-2,2-dimethylchroman-4-one
  参考文献：
  名称：

  Base-Induced Coupling of α-Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2-Azido-3-hydroxy Ketones, 2-Acylaziridines, and 2-Acylspiroaziridines

  摘要：

  DOI：

  10.1002/1099-0690(20021)2002:2<285::aid-ejoc285>3.0.co;2-j

文献信息

• Base-Induced Coupling of α-Azido Ketones with Aldehydes − An Easy and Efficient Route to Trifunctionalized Synthons 2-Azido-3-hydroxy Ketones, 2-Acylaziridines, and 2-Acylspiroaziridines
  作者：Tamás Patonay、Éva Juhász-Tóth、Attila Bényei

  DOI：10.1002/1099-0690(20021)2002:2<285::aid-ejoc285>3.0.co;2-j

  日期：2002.1
• Akuamoah, Robert K.; Brown, Philip E.; Marcus, Wafa Y., Journal of the Chemical Society. Perkin transactions I, 1995, p. 197 - 202
  作者：Akuamoah, Robert K.、Brown, Philip E.、Marcus, Wafa Y.、Steele, John E.

  DOI：——

  日期：——
• Discovery of Novel Benzopyranyl Tetracycles that Act as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand
  作者：Mingyan Zhu、Myung Hee Kim、Sanghee Lee、Su Jung Bae、Seong Hwan Kim、Seung Bum Park

  DOI：10.1021/jm1011269

  日期：2010.12.23

  A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-kappa B transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.