2-[2-(3-methylbutyl)indol-3-yl]-3,5,6-tribromocyclohexa-2,5-diene-1,4-dione | 244129-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[2-(3-methylbutyl)indol-3-yl]-3,5,6-tribromocyclohexa-2,5-diene-1,4-dione
• CAS: 244129-32-6
• 化学式: C₁₉H₁₆Br₃NO₂
• 分子量: 530.054
• InChiKey: GCQIPUFYNNCJSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.93
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-[2-(3-methylbutyl)indol-3-yl]-3,5,6-tribromocyclohexa-2,5-diene-1,4-dione 在 氢氧化钾 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 22.0h， 生成 2,5-bis[2-(3-methylbutyl)indol-3-yl]-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  A One-Pot, Two-Step Synthesis of Tetrahydro Asterriquinone E

  摘要：

  Bis(indolyl)dihydroxyquinone 2, the tetrahydro analogue of naturally occurring 1a, was synthesized by a novel, expeditious route. The short synthesis was accomplished by treating p-bromanil (3) with 2 equiv of indole 4 in the presence of cesium carbonate in acetonitrile at ambient temperature to provide a 1:1 mixture of the dibromo regioisomers 7 and 8, followed by hydrolysis of the mixture to afford 2, The synthetic compound 2 was found to inhibit the binding of the Grb2 adapter protein to tyrosine-phosphorylated EGF receptor (IC50 = 1.2 mu M).

  DOI：

  10.1021/ol990075b
• 作为产物：
  描述：

  2-Isopentyl-indol 、 四溴对苯醌 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以82%的产率得到2-[2-(3-methylbutyl)indol-3-yl]-3,5,6-tribromocyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  A One-Pot, Two-Step Synthesis of Tetrahydro Asterriquinone E

  摘要：

  Bis(indolyl)dihydroxyquinone 2, the tetrahydro analogue of naturally occurring 1a, was synthesized by a novel, expeditious route. The short synthesis was accomplished by treating p-bromanil (3) with 2 equiv of indole 4 in the presence of cesium carbonate in acetonitrile at ambient temperature to provide a 1:1 mixture of the dibromo regioisomers 7 and 8, followed by hydrolysis of the mixture to afford 2, The synthetic compound 2 was found to inhibit the binding of the Grb2 adapter protein to tyrosine-phosphorylated EGF receptor (IC50 = 1.2 mu M).

  DOI：

  10.1021/ol990075b