4-(4-chlorobut-2-ynoxy)-6-methylchromen-2-one | 177897-38-0

• 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-(4-chlorobut-2-ynoxy)-6-methylchromen-2-one
• CAS: 177897-38-0
• 化学式: C₁₄H₁₁ClO₃
• 分子量: 262.693
• InChiKey: SFMFJZFZSZZUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• 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-(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
• 作为产物：
  描述：

  4-羟基-6-甲基香豆素 、 1,4-二氯-2-丁炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 4-(4-chlorobut-2-ynoxy)-6-methylchromen-2-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 Thiopyrano[2,3-b][1]benzopyran-5(2H)-ones
  作者：Krishna C. Majumdar、Gour H. Jana

  DOI：10.3987/com-95-7307

  日期：——