tert-butyl N-[2-(5-hydroxy-1-benzofuran-3-yl)ethyl]-N-(2-nitrophenyl)sulfonylcarbamate | 949883-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[2-(5-hydroxy-1-benzofuran-3-yl)ethyl]-N-(2-nitrophenyl)sulfonylcarbamate
• CAS: 949883-00-5
• 化学式: C₂₁H₂₂N₂O₈S
• 分子量: 462.48
• InChiKey: YEFPKOPMLRENNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(5-hydroxy-1-benzofuran-3-yl)ethyl]-N-(2-nitrophenyl)sulfonylcarbamate 在 lithium hydroxide 、 巯基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以247 mg的产率得到
  参考文献：
  名称：

  1-Oxo-5-hydroxytryptamine:  A Surprisingly Potent Agonist of the 5-HT₃ (Serotonin) Receptor

  摘要：

  A novel synthetic route to 1-oxo-5-hydroxytryptamine, the benzofuran analogue of serotonin, has been developed. The new synthesis proceeds via the [3+2] cycloaddition of p-benzoquinone and 2,3-dihydrofuran, followed by a Lewis acid-catalyzed isomerization. This molecule proves to be a competent agonist (equipotent to serotonin) of the 5-HT3 receptor, demonstrating that the indolic proton of serotonin is not essential to its activation of the receptor.

  DOI：

  10.1021/ol071083s
• 作为产物：
  描述：

  1,2,3a,8b-Tetrahydrofuro[2,3-b][1]benzofuran-7-ol 在 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.5h， 生成 tert-butyl N-[2-(5-hydroxy-1-benzofuran-3-yl)ethyl]-N-(2-nitrophenyl)sulfonylcarbamate
  参考文献：
  名称：

  1-Oxo-5-hydroxytryptamine:  A Surprisingly Potent Agonist of the 5-HT₃ (Serotonin) Receptor

  摘要：

  A novel synthetic route to 1-oxo-5-hydroxytryptamine, the benzofuran analogue of serotonin, has been developed. The new synthesis proceeds via the [3+2] cycloaddition of p-benzoquinone and 2,3-dihydrofuran, followed by a Lewis acid-catalyzed isomerization. This molecule proves to be a competent agonist (equipotent to serotonin) of the 5-HT3 receptor, demonstrating that the indolic proton of serotonin is not essential to its activation of the receptor.

  DOI：

  10.1021/ol071083s

文献信息

• 1-Oxo-5-hydroxytryptamine:  A Surprisingly Potent Agonist of the 5-HT₃ (Serotonin) Receptor
  作者：Sean M. A. Kedrowski、Kiowa S. Bower、Dennis A. Dougherty

  DOI：10.1021/ol071083s

  日期：2007.8.1

  A novel synthetic route to 1-oxo-5-hydroxytryptamine, the benzofuran analogue of serotonin, has been developed. The new synthesis proceeds via the [3+2] cycloaddition of p-benzoquinone and 2,3-dihydrofuran, followed by a Lewis acid-catalyzed isomerization. This molecule proves to be a competent agonist (equipotent to serotonin) of the 5-HT3 receptor, demonstrating that the indolic proton of serotonin is not essential to its activation of the receptor.