5-(4,4-dimethyl-2-oxazolin-2-yl)-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran | 220658-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-(4,4-dimethyl-2-oxazolin-2-yl)-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran
• CAS: 220658-26-4
• 化学式: C₂₇H₃₁NO₅
• 分子量: 449.547
• InChiKey: JMJVNBAQRJGYNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  70.26
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(4,4-dimethyl-2-oxazolin-2-yl)-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran 在 4-二甲氨基吡啶 、 sodium hydroxide 、 2,4,6-三异丙基苯磺酰氯 、 三乙胺 、 碘甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-diphenylmethyl-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran-5-carboxamide
  参考文献：
  名称：

  A Convenient Synthesis of 2-Phenylbenzofuran Derivatives with Potent Testosterone 5a-Reductase Inhibitory Activities

  摘要：

  A convenient method for the synthesis of 4-[2-(benzo[b]furan-2-yl)phenyloxy]butyric acid derivatives with a carbamoyl group at the 5 or 6 position of the benzofuran ring showing potent 5 alpha-reductase inhibitory activities was developed. Oxazolin-2-ylbenzofuran derivatives were treated with tert-BuLi followed by tri(n-butyl)tin chloride, to give 2-tri(1-butyl)stannylbenzofuran derivatives. A palladium-catalyzed cross-coupling reaction of these benzofuran derivatives with tert-butyl 4-(2-iodophenyloxy)butyrate afforded the 2-phenyl benzofuran compounds in good yields.

  DOI：

  10.3987/com-98-8342
• 作为产物：
  描述：

  4-溴丁酸叔丁酯 在 四(三苯基膦)钯 sodium carbonate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.0h， 生成 5-(4,4-dimethyl-2-oxazolin-2-yl)-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran
  参考文献：
  名称：

  A Convenient Synthesis of 2-Phenylbenzofuran Derivatives with Potent Testosterone 5a-Reductase Inhibitory Activities

  摘要：

  A convenient method for the synthesis of 4-[2-(benzo[b]furan-2-yl)phenyloxy]butyric acid derivatives with a carbamoyl group at the 5 or 6 position of the benzofuran ring showing potent 5 alpha-reductase inhibitory activities was developed. Oxazolin-2-ylbenzofuran derivatives were treated with tert-BuLi followed by tri(n-butyl)tin chloride, to give 2-tri(1-butyl)stannylbenzofuran derivatives. A palladium-catalyzed cross-coupling reaction of these benzofuran derivatives with tert-butyl 4-(2-iodophenyloxy)butyrate afforded the 2-phenyl benzofuran compounds in good yields.

  DOI：

  10.3987/com-98-8342