2-(4-(triisopropylsiloxymethyl)phenyl)-5-(4-(methoxymethyl)phenyl)-3,4-bis-(4-bromophenyl)cyclopenta-2,4-dienone | 934667-50-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-(triisopropylsiloxymethyl)phenyl)-5-(4-(methoxymethyl)phenyl)-3,4-bis-(4-bromophenyl)cyclopenta-2,4-dienone
• 英文别名: 3,4-Bis(4-bromophenyl)-2-[4-(methoxymethyl)phenyl]-5-[4-[tri(propan-2-yl)silyloxymethyl]phenyl]cyclopenta-2,4-dien-1-one
• CAS: 934667-50-2
• 化学式: C₄₁H₄₄Br₂O₃Si
• 分子量: 772.692
• InChiKey: FDRBLFWWENKKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.15
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-(4-(triisopropylsiloxymethyl)phenyl)-5-(4-(methoxymethyl)phenyl)-3,4-bis-(4-bromophenyl)cyclopenta-2,4-dienone 、 二(4-溴苯基)乙炔 以 二苯醚 为溶剂， 以62.3%的产率得到1-(4-(triisopropylsiloxymethyl)phenyl)-4-(4-methoxymethylphenyl)-2,3,5,6-tetrakis-(4-bromophenyl)benzene
  参考文献：
  名称：

  Synthesis of Heterosubstituted Hexaarylbenzenes via Asymmetric Carbonylative Couplings of Benzyl Halides

  摘要：

  Asymmetric carbonylative couplings of benzyl halides have been shown to give heterosubstituted 1,3-diarylacetones in moderate to high yields. These asymmetric ketones were converted via Knoevenagel condensations to tetraarylcyclopentadienones, and further conversion via dehydro-Diels-Alder cycloadditions gave highly heterofunctionalized hexaarylbenzenes with uniquely functionalized aryl groups at the para positions of the central benzene. This method allows control of the substituents on each of four unique pendent aryl group positions, giving rise to substitution patterns not available using symmetrical 1,3-diarylacetones.

  DOI：

  10.1021/ol0629770
• 作为产物：
  描述：

  对苯二甲醇 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2-(4-(triisopropylsiloxymethyl)phenyl)-5-(4-(methoxymethyl)phenyl)-3,4-bis-(4-bromophenyl)cyclopenta-2,4-dienone
  参考文献：
  名称：

  Synthesis of Heterosubstituted Hexaarylbenzenes via Asymmetric Carbonylative Couplings of Benzyl Halides

  摘要：

  Asymmetric carbonylative couplings of benzyl halides have been shown to give heterosubstituted 1,3-diarylacetones in moderate to high yields. These asymmetric ketones were converted via Knoevenagel condensations to tetraarylcyclopentadienones, and further conversion via dehydro-Diels-Alder cycloadditions gave highly heterofunctionalized hexaarylbenzenes with uniquely functionalized aryl groups at the para positions of the central benzene. This method allows control of the substituents on each of four unique pendent aryl group positions, giving rise to substitution patterns not available using symmetrical 1,3-diarylacetones.

  DOI：

  10.1021/ol0629770

文献信息

• Synthesis of Heterosubstituted Hexaarylbenzenes via Asymmetric Carbonylative Couplings of Benzyl Halides
  作者：Robert G. Potter、Thomas S. Hughes

  DOI：10.1021/ol0629770

  日期：2007.3.1

  Asymmetric carbonylative couplings of benzyl halides have been shown to give heterosubstituted 1,3-diarylacetones in moderate to high yields. These asymmetric ketones were converted via Knoevenagel condensations to tetraarylcyclopentadienones, and further conversion via dehydro-Diels-Alder cycloadditions gave highly heterofunctionalized hexaarylbenzenes with uniquely functionalized aryl groups at the para positions of the central benzene. This method allows control of the substituents on each of four unique pendent aryl group positions, giving rise to substitution patterns not available using symmetrical 1,3-diarylacetones.