1-(2-Furyl)-3-(3-thienyl)-2-propen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-Furyl)-3-(3-thienyl)-2-propen-1-one
• 英文别名: (E)-1-(furan-2-yl)-3-thiophen-3-ylprop-2-en-1-one
• 化学式: C₁₁H₈O₂S
• 分子量: 204.249
• InChiKey: LIFFCYCWJGMLAV-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Furyl)-3-(3-thienyl)-2-propen-1-one 、 1-[2-氧-2-(2-吡啶基)乙基]碘化吡啶 在 乙酸铵 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  2,4,6-Trisubstituted pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship

  摘要：

  Designed and synthesized were a series of pyridines substituted at 2, 4, and 6 positions with various 5- or 6-memberd heteroaromatics as antitumor agents. They were evaluated their topoisomerase I and II inhibitory activities along with cytotoxicities against several human cancer cell lines. Among the prepared compounds, 10-20 showed significant topoisomerase I or II inhibitory activities, and 21-26 showed considerable cytotoxicities against several human cancer cell lines. Structure-activity relationship study indicates that 4-pyridine at 6-position of central pyridine plays a key role in biological activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.047
• 作为产物：
  描述：

  3-噻吩甲醛 、 2-乙酰基呋喃 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-(2-Furyl)-3-(3-thienyl)-2-propen-1-one
  参考文献：
  名称：

  2,4,6-Trisubstituted pyridines: Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship

  摘要：

  Designed and synthesized were a series of pyridines substituted at 2, 4, and 6 positions with various 5- or 6-memberd heteroaromatics as antitumor agents. They were evaluated their topoisomerase I and II inhibitory activities along with cytotoxicities against several human cancer cell lines. Among the prepared compounds, 10-20 showed significant topoisomerase I or II inhibitory activities, and 21-26 showed considerable cytotoxicities against several human cancer cell lines. Structure-activity relationship study indicates that 4-pyridine at 6-position of central pyridine plays a key role in biological activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.047

文献信息

• I2‐Promoted Oxidative Annulation of Deoxybenzoin‐Chalcone Adduct: Temperature‐Controlled Access to Tetrasubstituted 2,3‐trans‐Dihydrofurans and Furans
  作者：Thi Thanh Nhan Vu、Thu Ngoc Trinh、Thu Trang Pham、Minh Tu Ha、Dinh Hung Mac、Pascal Retailleau、Thanh Binh Nguyen

  DOI：10.1002/adsc.202400304

  日期：2024.6.18

  Tetrasubstituted 2,3‐trans‐dihydrofuran and furan are important heterocyclic scaffolds in natural product, bioorganic and medicinal chemistry as well as in material science. The synthesis of both of these heterocycles starting from common and readily available starting materials are challenging. We found that in situ generated deoxybenzoin‐chalcone Michael adducts underwent oxidative annulation upon heating

  四取代的2,3-反式二氢呋喃和呋喃是天然产物、生物有机和药物化学以及材料科学中重要的杂环支架。从常见且容易获得的起始材料开始合成这两种杂环具有挑战性。我们发现，原位生成的脱氧安息香-查耳酮迈克尔加合物在 DMSO 中与分子碘一起加热时发生氧化环化，在 80 °C 下选择性地提供 2,3-反式二氢呋喃，在 120 °C 下选择性地提供呋喃。