4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-ynyl)-2H-coumarin | 1099654-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-ynyl)-2H-coumarin
• 英文别名: 4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-yl)-2Hchromen-2-one；4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-ynyl)-2H-chromen-2-one；4-Hydroxy-3-[1-(4-methoxyphenyl)-3-phenylprop-2-ynyl]chromen-2-one；4-hydroxy-3-[1-(4-methoxyphenyl)-3-phenylprop-2-ynyl]chromen-2-one
• CAS: 1099654-08-6
• 化学式: C₂₅H₁₈O₄
• 分子量: 382.416
• InChiKey: AMJVZFCEXRYKFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-ynyl)-2H-coumarin 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到2-benzyl-3-(4-methoxyphenyl)-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Al(OTf)3-Catalyzed Preparation of 4-Hydroxy-3-propargylic ­Coumarins and Subsequent Regioselective Cyclization towards Furo- or Pyrano[3,2-c]coumarins

  摘要：

  An efficient and economical approach to functionalized furo[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives has been developed from 4-hydroxy-3-(prop-2-ynyl)coumarin derivatives through organocatalysis or metallo-organocatalysis. Selective 5-exo-dig' or 6-endo-dig' cyclization of the 4-hydroxy-3-(prop-2-ynyl)coumarin substrates could be achieved under organocatalytic {1,8-diazabicyclo[5.4.0]undec-7-ene} or metallo-organocatalytic (N-methylmorpholine/CuBr) conditions, respectively, to yield potentially bioactive heterocycles in excellent yields.

  DOI：

  10.1055/s-0034-1379971
• 作为产物：
  描述：

  4-羟基香豆素 、 1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-ol 在 aluminium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以91%的产率得到4-hydroxy-3-(1-(4-methoxyphenyl)-3-phenylprop-2-ynyl)-2H-coumarin
  参考文献：
  名称：

  Al(OTf)3-Catalyzed Preparation of 4-Hydroxy-3-propargylic ­Coumarins and Subsequent Regioselective Cyclization towards Furo- or Pyrano[3,2-c]coumarins

  摘要：

  An efficient and economical approach to functionalized furo[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives has been developed from 4-hydroxy-3-(prop-2-ynyl)coumarin derivatives through organocatalysis or metallo-organocatalysis. Selective 5-exo-dig' or 6-endo-dig' cyclization of the 4-hydroxy-3-(prop-2-ynyl)coumarin substrates could be achieved under organocatalytic {1,8-diazabicyclo[5.4.0]undec-7-ene} or metallo-organocatalytic (N-methylmorpholine/CuBr) conditions, respectively, to yield potentially bioactive heterocycles in excellent yields.

  DOI：

  10.1055/s-0034-1379971

文献信息

• Metal-Free, Adjustable, and Recyclable Catalytic Systems for the Construction of C–C Bonds by Activating Propargylic Alcohols
  作者：Ning Wang、Zengmin Li、Qin Hou、Feng Han、Yucai Yan、Jian Zhang、Chengxia Miao

  DOI：10.1021/acs.joc.2c01305

  日期：2022.9.2

  of active natural products and pharmaceutically relevant molecules have received increasing attention. However, developing an adjustable system for selectively synthesizing them is still a challenging task. Herein, sulfonic acid-functionalized ionic liquid was successfully used as the catalyst for the alkylation of 4-hydroxycoumarin derivatives with secondary aromatic propargylic alcohols using dimethyl

  吡喃[3,2- c]香豆素衍生物和C3-取代的4-羟基香豆素作为活性天然产物和药学相关分子的重要骨架结构越来越受到关注。然而，开发一个可调节的系统来选择性地合成它们仍然是一项具有挑战性的任务。在此，以碳酸二甲酯为绿色溶剂，磺酸功能化的离子液体成功地作为催化剂用于 4-羟基香豆素衍生物与仲芳炔丙醇的烷基化反应，收率高达 98%。另一方面，质子化咪唑基离子液体催化的环化反应也以接近定量的产率选择性地实现。开发的无金属催化体系具有良好的可调节性和可回收性，避免了金属和卤素的污染，减少反应后的中和，有利于催化剂与产物的分离。应用了新的策略来顺利进行克级反应。可调系统可能通过两种不同的机制发生，涉及炔丙基或丙二烯碳正离子以及催化剂和底物之间的氢键效应。