(E)-5-bromo-3-[3-(4-bromophenyl)acryloyl]tropolone | 1331961-68-2

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: (E)-5-bromo-3-[3-(4-bromophenyl)acryloyl]tropolone
• 英文别名: 5-Bromo-3-[3-(4-bromophenyl)acryloyl]-2-hydroxy-2,4,6-cycloheptatrien-1-one；5-bromo-3-[(E)-3-(4-bromophenyl)prop-2-enoyl]-2-hydroxycyclohepta-2,4,6-trien-1-one
• CAS: 1331961-68-2
• 化学式: C₁₆H₁₀Br₂O₃
• 分子量: 410.062
• InChiKey: QFPKXPFHEOFKSV-XVNBXDOJSA-N

物化性质

• 熔点：
  223-224 °C(Solv: methanol (67-56-1))
• 沸点：
  447.7±45.0 °C(Predicted)
• 密度：
  1.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-bromo-3-[3-(4-bromophenyl)acryloyl]tropolone 在 硫酸 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以62%的产率得到6-bromo-2-(4-bromophenyl)cyclohepta[b]pyran-4,9-dione
  参考文献：
  名称：

  A Facile Synthesis of New Troponoid-Bearing Flavonoid-Like Compounds

  摘要：

  A facile synthesis of a series of new flavonoid-like troponoid compounds, namely 3-(3-arylacryloyl)-5-bromotropolones (2a-i) and 2-aryl-6-bromocyclohepta[b]pyran-4,9-diones (3a-i) is described, involving the Claisen-Schmidt condensation reaction of 3-acetyl-5-bromotropolone (1) with various substituted benzaldehydes followed by the intramolecular oxidation cyclization reaction through the treatment with I-2/DMSO/H2SO4 system.

  DOI：

  10.3987/com-11-12223
• 作为产物：
  描述：

  对溴苯甲醛 、 3-acetyl-5-bromotropolone 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以83%的产率得到(E)-5-bromo-3-[3-(4-bromophenyl)acryloyl]tropolone
  参考文献：
  名称：

  A Facile Synthesis of New Troponoid-Bearing Flavonoid-Like Compounds

  摘要：

  A facile synthesis of a series of new flavonoid-like troponoid compounds, namely 3-(3-arylacryloyl)-5-bromotropolones (2a-i) and 2-aryl-6-bromocyclohepta[b]pyran-4,9-diones (3a-i) is described, involving the Claisen-Schmidt condensation reaction of 3-acetyl-5-bromotropolone (1) with various substituted benzaldehydes followed by the intramolecular oxidation cyclization reaction through the treatment with I-2/DMSO/H2SO4 system.

  DOI：

  10.3987/com-11-12223

文献信息

• A Facile Synthesis of New Troponoid-Bearing Flavonoid-Like Compounds
  作者：Wentao Gao、Yang Li、Mingqin Chang

  DOI：10.3987/com-11-12223

  日期：——

  A facile synthesis of a series of new flavonoid-like troponoid compounds, namely 3-(3-arylacryloyl)-5-bromotropolones (2a-i) and 2-aryl-6-bromocyclohepta[b]pyran-4,9-diones (3a-i) is described, involving the Claisen-Schmidt condensation reaction of 3-acetyl-5-bromotropolone (1) with various substituted benzaldehydes followed by the intramolecular oxidation cyclization reaction through the treatment with I-2/DMSO/H2SO4 system.