2,4-diphenyl-4H-chromene | 53209-37-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2,4-diphenyl-4H-chromene
• 英文别名: 4-phenylflav-2-ene；2,4-diphenyl-4H-chromene；2,4-Diphenyl-4H-chromen；2,4-Diphenyl-4H-benzopyran；2,4-Diphenyl-4H-chromen；4-Phenyl-flav-2-en
• CAS: 53209-37-3；1005391-57-0
• 化学式: C₂₁H₁₆O
• 分子量: 284.357
• InChiKey: PZZKQIVCCJKOFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-diphenyl-4H-chromene 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.58h， 生成 2,4-diphenyl-3-dimethylaminomethyl-4H-chromene
  参考文献：
  名称：

  Koblic, A. V.; Suzdalev, K. F., Journal of Organic Chemistry USSR (English Translation), 1989, p. 155 - 158

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-羟基苯基)-1,3-二苯基-1-丙酮 在 三氟乙酸 作用下， 反应 12.0h， 以99%的产率得到2,4-diphenyl-4H-chromene
  参考文献：
  名称：

  TFA-Mediated Tandem Friedel−Crafts Alkylation/Cyclization/Hydrogen Transfer Process for the Synthesis of Flavylium Compounds

  摘要：

  [Graphics]The tandem reaction of phenols and chalcones in refluxing TFA gave the flavylium species of 2-hydroxy-2-phenyl-2H-chromenes in moderate to good isolated yields. The reaction was proposed to involve a tandem transformation of Friedel-Crafts alkylation, dehydrative cyclization, intermolecular hydrogen transfer, and hydration. As a multifunctional catalyst, TFA mediated the processes efficiently and cleanly.

  DOI：

  10.1021/jo7015604

文献信息

• Shedding Light on Organocatalysis-Light-Assisted Asymmetric Ion-Pair Catalysis for the Enantioselective Hydrogenation of Pyrylium Ions
  作者：Chien-Chi Hsiao、Hsuan-Hung Liao、Erli Sugiono、Iuliana Atodiresei、Magnus Rueping

  DOI：10.1002/chem.201300766

  日期：2013.7.22

  A new light‐driven asymmetric ion‐pair catalysis procedure for the metal‐free enantioselective hydrogenation of in situ generated pyrylium ions from readily available chalcones was developed (see scheme). The photo‐assisted Brønsted acid catalyzed procedure has broad scope and allows, for the first time, access to valuable 4H‐chromenes in good yields and with excellent enantioselectivities.

  开发了一种新的光驱动不对称离子对催化程序，用于从容易获得的查耳酮中就地生成的吡啶离子进行无金属对映选择性加氢（参见方案）。光辅助的布朗斯台德酸催化方法具有广泛的应用范围，并且首次允许以高收率和优异的对映选择性获得有价值的4 H-色烯。
• Synthesis, in vitro and in vivo evaluation of 2-aryl-4H-chromene and 3-aryl-1H-benzo[f]chromene derivatives as novel α-glucosidase inhibitors
  作者：Alexander A. Spasov、Denis A. Babkov、Dmitry V. Osipov、Vladlen G. Klochkov、Diana R. Prilepskaya、Maxim R. Demidov、Vitaly A. Osyanin、Yuri N. Klimochkin

  DOI：10.1016/j.bmcl.2018.10.018

  日期：2019.1

  report a study of novel arylchromene derivatives as analogs of naturally occurring flavonoids with prominent α-glucosidase inhibitory properties. Novel inhibitors were identified via simple stepwise in silico screening, efficient synthesis, and biological evaluation. It is shown that 2-aryl-4H-chromene core retains pharmacophore properties while being readily available synthetically. A lead compound

  在本文中，我们报告了一种新型的芳基亚甲基衍生物的研究，该衍生物是具有突出的α-葡萄糖苷酶抑制特性的天然类黄酮的类似物。通过简单的逐步计算机筛选，有效合成和生物学评估来鉴定新型抑制剂。显示2-芳基-4H-亚甲基核心保留药效基团性质，同时易于合成获得。通过筛选鉴定出的先导化合物可抑制酵母α-葡萄糖苷酶，IC 50为62.26 µM，可防止2.2 mg / kg剂量的大鼠餐后高血糖。
• Scandium (III)-Catalyzed Cycloaddition of <i>in situ</i> Generated <i>ortho</i> -Quinone Methides with Vinyl Azides: An Efficient Access to Substituted 4<i>H</i> -Chromenes
  作者：Nuligonda Thirupathi、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1002/adsc.201800565

  日期：2018.9.17

  convenient and practical synthesis of 4H‐chromenes from the readily accessible o‐hydroxybenzhydryl alcohols and vinyl azides has been achieved. The transformation proceeds through a cascade that involves formation of an ortho‐quinone methide, [4+2]‐cycloaddition and elimination of hydrazoic acid. The reaction is well tolerated with respect to both the o‐hydroxybenzhydrols and the vinyl azides and affords

  从容易获得的邻羟基苯二甲醇和叠氮化物实现了4 H-色烯的便捷，实用合成。转化过程通过级联反应进行，该级联反应包括形成邻苯二甲酰甲基甲烷，[4 + 2]-环加成反应和消除酸。该反应对邻羟基苯酚和叠氮化乙烯都具有良好的耐受性，并能以中等至良好的收率提供产物。
• Essential Rule Derived from Thermodynamics and Kinetics Studies of Benzopyran Compounds
  作者：Baolong Chen、Xin Hu、Xiaoqing Zhu

  DOI：10.3390/molecules28248039

  日期：——

  Compounds with benzopyran as the core structure play an important role in the total synthesis of antioxidants, drugs, and natural products. Herein, the thermodynamic data of benzopyran compounds and their intermediates were measured and calculated by combining thermodynamics with kinetics. The mechanism of reactions between four benzopyran compounds and organic hydride acceptors was proven to be a

  以苯并吡喃为核心结构的化合物在抗氧化剂、药物和天然产物的全合成中发挥着重要作用。本文通过热力学与动力学相结合的方法，测量并计算了苯并吡喃类化合物及其中间体的热力学数据。四种苯并吡喃化合物与有机氢化物受体之间的反应机理被证明是一步氢化物转移。阐明了这些化合物及其相应中间体的热力学性质。证明了电化学测量方法的合理性和准确性。此外，如先前的研究所示，研究了苯环上的 C-H 键和对位取代基常数之间存在的独特结构的基本规则。氢化物转移反应发现了热力学和动力学之间的同时相关性，其中反应位点通过苯环、双键或N原子与取代基连接。热力学和动力学之间存在相关性的可能原因是苯环、双键或N原子具有转移电子效应的作用。这一发现可应用于氢化物自交换反应活化能的计算、动力学同位素效应的预测以及此类有机氢化物中氢化物转移选择性还原过程的探索。
• Bird, T. Geoffrey C.; Brown, Ben R.; Stuart, Ian A., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1831 - 1846
  作者：Bird, T. Geoffrey C.、Brown, Ben R.、Stuart, Ian A.、Tyrrell, William R.

  DOI：——

  日期：——