3-iodo-2-(thiophen-3-yl)-4,5,6,7-tetrahydrobenzofuran-4-ol | 1381891-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-iodo-2-(thiophen-3-yl)-4,5,6,7-tetrahydrobenzofuran-4-ol
• CAS: 1381891-03-7
• 化学式: C₁₂H₁₁IO₂S
• 分子量: 346.189
• InChiKey: JCJMEHALBIHCNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-iodo-2-(thiophen-3-yl)-4,5,6,7-tetrahydrobenzofuran-4-ol 、 苯并-1,4-二氧六环-6-硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以61%的产率得到3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(thiophen-3-yl)-4,5,6,7-tetrahydrobenzofuran-4-ol
  参考文献：
  名称：

  Solution-Phase Synthesis of a Highly Substituted Furan Library

  摘要：

  A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

  DOI：

  10.1021/co300040q
• 作为产物：
  描述：

  2-(thiophen-3-ylethynyl)cyclohex-2-en-1-one 在 水 、 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以68%的产率得到3-iodo-2-(thiophen-3-yl)-4,5,6,7-tetrahydrobenzofuran-4-ol
  参考文献：
  名称：

  Solution-Phase Synthesis of a Highly Substituted Furan Library

  摘要：

  A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.

  DOI：

  10.1021/co300040q