9-(2-methoxyphenyl)naphtho[2,3-c]furan-1(3H)-one | 1051385-19-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 9-(2-methoxyphenyl)naphtho[2,3-c]furan-1(3H)-one
• 英文别名: 4-(2-methoxyphenyl)-1H-benzo[f][2]benzofuran-3-one
• CAS: 1051385-19-3
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: IUUHYQHEMFMPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氧化碳 、 2-乙炔基苯甲醚 、 potassium carbonate 、 1-bromo-3-phenylprop-2-yne 在 silver(I) iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以27.6%的产率得到8-methoxy-4-phenylnaphtho[2,3-c]firan-1(3H)-one
  参考文献：
  名称：

  Silver-Catalyzed One-Pot Synthesis of Arylnaphthalene Lactones

  摘要：

  Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied.

  DOI：

  10.1021/jo801213m

文献信息

• Silver-Catalyzed One-Pot Synthesis of Arylnaphthalene Lactones
  作者：Nicolas Eghbali、Jennifer Eddy、Paul T. Anastas

  DOI：10.1021/jo801213m

  日期：2008.9.1

  Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied.