1-bromo-3,4,6-trihydroxy-5-oxo-5H-benzocycloheptene-8-carboxylic acid | 91267-96-8

• 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: 1-bromo-3,4,6-trihydroxy-5-oxo-5H-benzocycloheptene-8-carboxylic acid
• 英文别名: 4'-Brom-1',2'-dihydroxy-benzotropolon-4-carbonsaeure；1-Bromo-3,4,5-trihydroxy-6-oxobenzo[7]annulene-8-carboxylic acid
• CAS: 91267-96-8
• 化学式: C₁₂H₇BrO₆
• 分子量: 327.088
• InChiKey: PVJFWWKLDPDPRA-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 沸点：
  576.5±50.0 °C(Predicted)
• 密度：
  2.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-bromo-3,4,6-trihydroxy-5-oxo-5H-benzocycloheptene-8-carboxylic acid 在 四丁基氯化铵 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (E)-3-(8-carboxy-3,4,6-trihydroxy-5-oxo-5H-benzocyclohepten-1-yl)-2-propenoic acid
  参考文献：
  名称：

  Crocipodin, a benzotropolone pigment from the mushroom Leccinum crocipodium (Boletales)

  摘要：

  Crocipodin, an unusual benzotropolone pigment, has been isolated from the fruit bodies of the mushroom Leccinum crocipodium. Its structure was determined by spectroscopic methods, particularly 2D NMR spectroscopy. The structure was confirmed by total synthesis, starting from 4-bromocatechol and gallic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.060
• 作为产物：
  描述：

  4-溴邻苯二酚 、 没食子酸 在 horseradish peroxidase type I 、 双氧水 作用下， 以 丙酮 为溶剂， 以75%的产率得到1-bromo-3,4,6-trihydroxy-5-oxo-5H-benzocycloheptene-8-carboxylic acid
  参考文献：
  名称：

  Crocipodin, a benzotropolone pigment from the mushroom Leccinum crocipodium (Boletales)

  摘要：

  Crocipodin, an unusual benzotropolone pigment, has been isolated from the fruit bodies of the mushroom Leccinum crocipodium. Its structure was determined by spectroscopic methods, particularly 2D NMR spectroscopy. The structure was confirmed by total synthesis, starting from 4-bromocatechol and gallic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.060

文献信息

• Crocipodin, a benzotropolone pigment from the mushroom Leccinum crocipodium (Boletales)
  作者：Lydia Kerschensteiner、Florian Löbermann、Wolfgang Steglich、Dirk Trauner

  DOI：10.1016/j.tet.2010.12.060

  日期：2011.2

  Crocipodin, an unusual benzotropolone pigment, has been isolated from the fruit bodies of the mushroom Leccinum crocipodium. Its structure was determined by spectroscopic methods, particularly 2D NMR spectroscopy. The structure was confirmed by total synthesis, starting from 4-bromocatechol and gallic acid. (C) 2010 Elsevier Ltd. All rights reserved.