4-chloromethylpyrano[3,2-c][1]benzopyran-5(2H)-one | 944059-72-7

• 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-chloromethylpyrano[3,2-c][1]benzopyran-5(2H)-one
• CAS: 944059-72-7
• 化学式: C₁₄H₁₁ClO₃
• 分子量: 262.693
• InChiKey: QWVOKNNKJWLBJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chloromethylpyrano[3,2-c][1]benzopyran-5(2H)-one 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 、 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 、 苯 为溶剂， 生成 (1R,14S)-8,17,19-trimethyl-4,12,21-trioxapentacyclo[12.8.0.02,11.05,10.015,20]docosa-2(11),5(10),6,8,15,17,19-heptaen-3-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
• 作为产物：
  描述：

  4-(4-chlorobut-2-ynoxy)-6-methylchromen-2-one 以 氯苯 为溶剂， 反应 16.0h， 生成 4-chloromethylpyrano[3,2-c][1]benzopyran-5(2H)-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

文献信息

• Regioselective synthesis of heterocyclic scaffold by aryl radical cyclization
  作者：K. C. Majumdar、N. Kundu

  DOI：10.1002/jhet.5570450414

  日期：2008.7

  Regioselective synthesis of a number of coumarin-annulated pentacyclic heterocycles have been achieved by tri-n-butyltin hydride-mediated aryl radical cyclization. The products are formed as a mixture of cis- and trans- forms which were successfully separated by careful silica gel flash chromatography.

  许多香豆素-环五环杂环的区域选择性合成已经由三-实现Ñ -butyltin氢化物介导的芳基环化。产物以顺式和反式形式的混合物形式形成，可通过仔细的硅胶快速色谱法成功分离。