N-diphenylmethyl-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran-5-carboxamide | 220658-30-0

• 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: N-diphenylmethyl-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran-5-carboxamide
• 英文别名: tert-butyl 4-[2-[5-(benzhydrylcarbamoyl)-1-benzofuran-2-yl]phenoxy]butanoate
• CAS: 220658-30-0
• 化学式: C₃₆H₃₅NO₅
• 分子量: 561.678
• InChiKey: LTLYRIFZBYQWAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-diphenylmethyl-2-<2-<3-(tert-butyl)oxycarbonyl-1-propyloxy>phenyl>benzofuran-5-carboxamide 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以94%的产率得到4-<2-<5-(N-diphenylmethylcarbamoyl)benzofuran-2-yl>phenyloxy>butyric acid
  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：

  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