4-[(2-bromo-4-methylphenoxy)methyl]-2H-pyrano[3,2-c]chromen-5-one | 944059-77-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-[(2-bromo-4-methylphenoxy)methyl]-2H-pyrano[3,2-c]chromen-5-one
• CAS: 944059-77-2
• 化学式: C₂₀H₁₅BrO₄
• 分子量: 399.241
• InChiKey: SGXVEACDBGLSFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(2-bromo-4-methylphenoxy)methyl]-2H-pyrano[3,2-c]chromen-5-one 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 苯 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  C‐C Bond Formation by Radical Cyclization: Regioselective Synthesis of [6,6] Pyrano pyran System

  摘要：

  A number of 4-aryloxymethyl pyrano[3,2-c][1]benzopyran-5-(2H)-ones 3(a-f) were prepared by refluxing 4-chloromethyl pyrano[3,2c][1] benzopyran-5-(2H)-ones 1(a,b) with o-bromophenols 2(a-c) in acetone in the presence of anhydrous potassium carbonate and sodium iodide in 70-80% yield. Compounds 3(a-f) were then subjected to radical cyclization by refluxing with tri-n-butyltin chloride, sodium cyanoborohydride, and azobisisobutyronitrile (AIBN) in dry benzene for 4-5 h to give a cis-diastereomeric mixture of [6,6] pyranopyran derivatives in 80-85% yield.

  DOI：

  10.1080/00397910701266125
• 作为产物：
  描述：

  1-chloro-4-(4'-coumarinylopxy)-but-2-yne 在 potassium carbonate 、 sodium iodide 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 16.0h， 生成 4-[(2-bromo-4-methylphenoxy)methyl]-2H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  C‐C Bond Formation by Radical Cyclization: Regioselective Synthesis of [6,6] Pyrano pyran System

  摘要：

  A number of 4-aryloxymethyl pyrano[3,2-c][1]benzopyran-5-(2H)-ones 3(a-f) were prepared by refluxing 4-chloromethyl pyrano[3,2c][1] benzopyran-5-(2H)-ones 1(a,b) with o-bromophenols 2(a-c) in acetone in the presence of anhydrous potassium carbonate and sodium iodide in 70-80% yield. Compounds 3(a-f) were then subjected to radical cyclization by refluxing with tri-n-butyltin chloride, sodium cyanoborohydride, and azobisisobutyronitrile (AIBN) in dry benzene for 4-5 h to give a cis-diastereomeric mixture of [6,6] pyranopyran derivatives in 80-85% yield.

  DOI：

  10.1080/00397910701266125