9-methyl-2-phenyl-4-p-tolylpyrano[3,2-c]chromen-5(4H)-one | 1337926-57-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-methyl-2-phenyl-4-p-tolylpyrano[3,2-c]chromen-5(4H)-one
• 英文别名: 9-methyl-4-(4-methylphenyl)-2-phenyl-4H-pyrano[3,2-c]chromen-5-one
• CAS: 1337926-57-4
• 化学式: C₂₆H₂₀O₃
• 分子量: 380.443
• InChiKey: YEAKZQCPDIEHKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-甲基苯基)-3-苯基丙-2-炔-1-醇 在 N-甲基吗啉 、 aluminium(III) triflate 、 copper(I) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 9-methyl-2-phenyl-4-p-tolylpyrano[3,2-c]chromen-5(4H)-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

文献信息

• KF/clinoptilolite nanoparticles as a novel catalyst for the green synthesis of chromens using three component reactions of 4‐hydroxycoumarins: Study of antioxidant activity
  作者：Samanehsadat Sharifi、Malek Taher Maghsoudlou、Nourallah Hazeri、Faramarz Rostami‐Charati

  DOI：10.1002/jccs.201800282

  日期：2019.10

  In this research, the green synthesis of chromen derivatives in good yields is described via three‐component reactions of 4‐hydroxycumarine, aldehydes or ketones, and methyl ketones in the presence of KF/clinoptilolite nanoparticles (KF/CP‐NPs) under solvent‐free conditions at 50°C in low time. The present methodology suggests some advantages such as low reaction time, easy and simple procedure, green

  在这项研究中，描述了在溶剂中存在KF /斜发沸石纳米粒子（KF / CP-NPs）的情况下，通过4-羟基异丙胺，醛或酮和甲基酮的三组分反应，高产率地合成了铬衍生物的绿色合成方法。低温条件下在50°C下保持自由状态 本方法论提出了一些优点，例如反应时间短，方法简便，绿色方法，催化剂便宜，产物收率高以及存在用于进行这些反应的不同底物。另外，应该提到的是，通过DPPH自由基捕获和还原铁离子的电位测试，然后将结果与作为合成抗氧化剂的TBHQ和BHT进行了比较，研究了一些制备的化合物（例如4a–4d）的抗氧化剂活性。在这项研究中，化合物图4c显示具有适度的DPPH自由基捕获，并且化合物4b和4d显示出良好的三价铁离子还原能力。
• Soluble Glass, an Efficient Promoter for the Cascade Addition-Cyclization Reaction of 4-Hydroxycoumarins to Chalcone Derivatives
  作者：Mojtaba Lashkari、Majid Ghashang、Ali Abedi-Madiseh

  DOI：10.1080/00304948.2020.1833694

  日期：2021.1.2

  (2021). Soluble Glass, an Efficient Promoter for the Cascade Addition-Cyclization Reaction of 4-Hydroxycoumarins to Chalcone Derivatives. Organic Preparations and Procedures International: Vol. 53, No. 1, pp. 52-58.

  （2021年）。可溶性玻璃，4-羟基香豆素与查尔酮衍生物的级联加成环化反应的有效促进剂。国际有机制剂和程序：第 53，第1号，第52-58页。
• Gold(III)-Catalyzed Tandem Conjugate Addition/Annulation of 4-Hydroxycoumarins with α,β-Unsaturated Ketones
  作者：Yunkui Liu、Jie Zhu、Jianqiang Qian、Bo Jiang、Zhenyuan Xu

  DOI：10.1021/jo201342m

  日期：2011.11.4

  efficient and selective approach for the synthesis of functionalized pyranocoumarins has been developed via a gold(III)-catalyzed tandem conjugate addition/annulation reaction of 4-hydroxycoumarins with α,β-unsaturated ketones.

  通过4-羟基香豆素与α，β-不饱和酮的金（III）催化的串联共轭加成/环化反应，已经开发了一种有效且选择性的功能化吡喃香豆素的合成方法。
• Al(OTf)3-Catalyzed Preparation of 4-Hydroxy-3-propargylic ­Coumarins and Subsequent Regioselective Cyclization towards Furo- or Pyrano[3,2-c]coumarins
  作者：Barend Bezuidenhoudt、Sudipta Ponra、Mukut Gohain、Johannes van Tonder

  DOI：10.1055/s-0034-1379971

  日期：——

  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.