diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate | 188357-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate
• CAS: 188357-92-8
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: FNHINXMSNFSJBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate 以 四氢呋喃 、 甲醇 为溶剂， 以35.6 %的产率得到tetraethyl 2,4,8,10-tetramethyl-6,12-bis(4-hydroxyphenyl)-3,9-dioxapentacyclo[6.4.0.0^2,7.0^4,11.0^5,10]dodecane-1,5,7,11-tetracarboxylate
  参考文献：
  名称：

  洞察 4-aryl-4H-pyran 的光化学反应：实验和理论研究

  摘要：

  在本文中，我们研究了 4-aryl-4 H - pyran 的光化学反应，发现结构对称性对其光化学行为有重要影响。当使用对称的 4-aryl-4 H - pyran 时，例如 2,6-dimethyl-4-aryl-4 H -pyran-3,5-dicarboxylate 二乙酯，主要进行 [2 + 2] 光环加成反应。而不对称的 4- aryl-4 H -pyran，如 2-amino-3-cyano-4-aryl-4 H - pyran，主要进行光裂解反应。为了推测反应机理，在B3LYP-D3/def2TZVP//B3LYP-D3/6-31G(d)水平进行了密度泛函理论（DFT）和时间相关密度泛函理论（TDDFT）计算。结果表明，二乙基 2,6-二甲基-4-aryl-4H -pyran-3,5-dicarboxylate 经过两步 [2 + 2] 光环加成，通过分子间和分子内反应得到 3

  DOI：

  10.1016/j.tet.2022.133212
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对羟基苯甲醛 在 乙酸酐 、 zinc(II) chloride 作用下， 生成 diethyl 4-(4-hydroxyphenyl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate
  参考文献：
  名称：

  洞察 4-aryl-4H-pyran 的光化学反应：实验和理论研究

  摘要：

  在本文中，我们研究了 4-aryl-4 H - pyran 的光化学反应，发现结构对称性对其光化学行为有重要影响。当使用对称的 4-aryl-4 H - pyran 时，例如 2,6-dimethyl-4-aryl-4 H -pyran-3,5-dicarboxylate 二乙酯，主要进行 [2 + 2] 光环加成反应。而不对称的 4- aryl-4 H -pyran，如 2-amino-3-cyano-4-aryl-4 H - pyran，主要进行光裂解反应。为了推测反应机理，在B3LYP-D3/def2TZVP//B3LYP-D3/6-31G(d)水平进行了密度泛函理论（DFT）和时间相关密度泛函理论（TDDFT）计算。结果表明，二乙基 2,6-二甲基-4-aryl-4H -pyran-3,5-dicarboxylate 经过两步 [2 + 2] 光环加成，通过分子间和分子内反应得到 3

  DOI：

  10.1016/j.tet.2022.133212

文献信息

• Synthesis and Biological Evaluation of 3,9-Dioxatetraasteranes as <i>C</i><sub>2</sub>-Symmetric HIV-1 Protease Inhibitors and Docking Study
  作者：Peng Li、Shijie Wang、Huiqin Wang、Hong Yan

  DOI：10.1248/bpb.b18-00705

  日期：2019.2.1

  A series of tetraethyl 2,4,8,10-tetramethyl-6,12-diaryl-3,9-dioxahexacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5,7,11-tetracarboxylates (simplified as 3,9-dioxatetraasteranes) with C2-symmetric structural characteristics were synthesized through the [2 + 2] photocycloaddition of the diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates. Besides, their anti-human immunodeficiency virus (HIV)-1 activities were evaluated by enzyme-linked immunosorbent assay (ELISA) assay against HIV-1 (IIIB) replication in MT-4 cell culture. The result showed that the tested compounds exhibited potential activates with IC50 values less than 110 nM. Furthermore, docking study was carried out to study the binding mode of these compounds. The results indicated that the overall orientation of the inhibitors in the active site were similar to that of the cyclic urea AHA001 and a hydrogen bond with the protein residues might play a crucial role in their anti-HIV-1 activities. Such results will provide a theoretical foundation for further investigations on the biological activity of 3,9-dioxatetraasteranes.

  一系列具有 C2 对称结构特征的 2,4,8,10-四甲基-6,12-二芳基-3,9-二氧杂六环[6.4.0.02,7.04,11.通过 2,6-二甲基-4-芳基-4H-吡喃-3,5-二甲酸二乙酯的[2 + 2]光环加成反应，合成了具有 C2 对称结构特征的十二烷-1,5,7,11-四羧酸盐（简化为 3,9-二氧杂四烷烃）。此外，还通过酶联免疫吸附试验（ELISA）评估了这些化合物在 MT-4 细胞培养中对 HIV-1 (IIIB) 复制的抗人类免疫缺陷病毒（HIV）-1 活性。结果表明，受试化合物具有潜在的活性，其 IC50 值小于 110 nM。此外，还对这些化合物的结合模式进行了对接研究。结果表明，抑制剂在活性位点的整体取向与环状脲 AHA001 相似，与蛋白质残基的氢键可能在它们的抗 HIV-1 活性中起着关键作用。这些结果将为进一步研究 3,9-二氧四酰胺类化合物的生物活性提供理论基础。
• Synthesis and Biological Evaluation of 3,9-Dioxatetraasteranes as Potential Inhibitors of Epidermal Growth Factor Receptor
  作者：Hong Yan、Hongjun Wang、Nana Tian、Dongchen Chu

  DOI：10.2174/1570180819666220928151144

  日期：2022.9.28

  Epidermal growth factor receptor (EGFR) is a validated and therapeutically amenable target, and inhibition of the EGFR signaling pathway has emerged as an attractive target for cancer therapy.

  The present work was designed to synthesize and evaluate the antiproliferative activity activity of a novel series of 3,9-dioxatetraasteranes as potential inhibitors of EGFR. All target compounds were evaluated for antiproliferative activity in vitro against A549 and HepG2 cell lines.

  Among the target compounds, compound B13 displayed the most potent antiproliferative activity against A549 with IC50 = 4.31 μM and HepG2 with IC50 = 6.92 μM. In addition, a molecular docking study was performed to investigate the binding mode and binding capacity with EGFR (PDB code: 1M17).

  The results indicated that 3,9-dioxatetraasteranes may be promising potential EGFR inhibitors.

  背景： 表皮生长因子受体（表皮生长因子受体，EGFR）是一个已被证实且可用于治疗的靶点，抑制表皮生长因子受体信号通路已成为癌症治疗的一个有吸引力的靶点。 方法： 本研究旨在合成和评估一系列新型 3,9-二氧四酰胺类化合物作为表皮生长因子受体潜在抑制剂的抗增殖活性。所有目标化合物都针对 A549 和 HepG2 细胞系进行了体外抗增殖活性评估。 结果显示 在目标化合物中，化合物 B13 对 A549 的抗增殖活性最强（IC50 = 4.31 μM），对 HepG2 的抗增殖活性最强（IC50 = 6.92 μM）。此外，还进行了分子对接研究，以探讨与表皮生长因子受体（PDB 代码：1M17）的结合模式和结合能力。 结果表明 研究结果表明，3,9-二氧四酰胺类化合物可能是很有潜力的表皮生长因子受体抑制剂。
• SnCl2/nano SiO2: A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans
  作者：Javad Safaei-Ghomi、Raheleh Teymuri、Hossein Shahbazi-Alavi、Abolfazl Ziarati

  DOI：10.1016/j.cclet.2013.06.021

  日期：2013.10

  A highly efficient and general method for the synthesis of polyfunctionalized 4H-pyrans is established through a one-pot multicomponent cyclocondensation of aromatic aldehydes with CH acids, malononitrile and ethyl acetoacetate using nano silica supported tin (II) chloride as a catalyst. In this method SnCl2/nano SiO2 was used as green and reusable catalyst. Excellent yields, short reaction times, simple workup, and inexpensiveness and commercially availability of the catalyst are the advantages of this method. (C) 2013 Javad Safaei-Ghomi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Improved synthesis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation
  作者：Cheng-Liang Ni、Xiao-Hui Song、Hong Yan、Xiu-Qing Song、Ru-Gang Zhong

  DOI：10.1016/j.ultsonch.2009.09.006

  日期：2010.2

  Diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates (1) have been synthesized by the reaction of aryl aldehyde and 1,3-diketone catalyzed by ZnCl2 under ultrasound irradiation. The effects of changes in the ultrasonic power, temperature, and reaction time are discussed. With the optimized reaction conditions, various aryl aldehydes were used to synthesize 4H-pyrans (1) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time and high yield of product. (C) 2009 Elsevier B.V. All rights reserved.
• A novel photodimerization of 4-aryl-4H-pyrans for cage compounds
  作者：Hongxing Xin、Xiaohe Zhu、Hong Yan、Xiuqing Song

  DOI：10.1016/j.tetlet.2013.04.016

  日期：2013.6

  Irradiation of 4-aryl-4H-pyrans in either the solid state or in solution gave rise to the formation of novel oxa-cage compounds, 3,9-dioxatetraasteranes, derived from a double [2 + 2] cycloaddition reaction. Meanwhile, an unexpected oxetane formed by the Paterno-Buchi reaction of benzophenone with the pyrans, was established by H-1 NMR data as well as by X-ray crystallographic analysis. Experimental observations and theoretical calculations confirmed that the photodimerization was effectively catalyzed by the triplet excited state of benzophenone, while the Paterno-Buchi reaction was competitive with the process. (C) 2013 Elsevier Ltd. All rights reserved.