6-bromo-2,2-bis-(4-methoxyphenyl)-2H-[1]benzopyran | 1338224-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-bromo-2,2-bis-(4-methoxyphenyl)-2H-[1]benzopyran
• 英文别名: 6-Bromo-2,2-bis(4-methoxyphenyl)chromene；6-bromo-2,2-bis(4-methoxyphenyl)chromene
• CAS: 1338224-82-0
• 化学式: C₂₃H₁₉BrO₃
• 分子量: 423.306
• InChiKey: IMIWZQZIDOICMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 6-bromo-2,2-bis-(4-methoxyphenyl)-2H-[1]benzopyran 在 potassium phosphate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以30%的产率得到2-[1,1-bis-(4-methoxyphenyl)methyl]-5-styrylbenzo[b]furan
  参考文献：
  名称：

  The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran

  摘要：

  The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1]benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.05.005
• 作为产物：
  描述：

  4-溴苯酚 、 1,1-双(4-甲氧基苯基)-2-丙炔-1-醇 在 aluminium oxide (activated, acidic, Brockmann 1, ~150 #) 作用下， 以 甲苯 为溶剂， 以27%的产率得到6-bromo-2,2-bis-(4-methoxyphenyl)-2H-[1]benzopyran
  参考文献：
  名称：

  The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran

  摘要：

  The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1]benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.05.005

文献信息

• The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran
  作者：Christopher D. Gabbutt、B. Mark Heron、Colin Kilner、Suresh B. Kolla

  DOI：10.1016/j.dyepig.2011.05.005

  日期：2012.2

  The ligand-free Pd-mediated reaction between styrene and a 6-bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diarylmethyl)-5-styrylbenzofuran via a tandem Heck coupling - ring-contraction process; none of the styryl substituted 2,2-diaryl-2H-[1]benzopyran was observed. A 2,2-diaryl-6-styryl-2H-[1]benzopyran resulted from the condensation between 4-hydroxystilbene and a 1,1-diarylpropynol and which exhibited photochromism through the reversible electrocyclisation of the pyran unit; no isomerisation - electrocyclisation of the stilbene moiety was detected. (C) 2011 Elsevier Ltd. All rights reserved.