3,3'-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one) | 82420-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3'-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)
• 英文别名: 2-Hydroxy-3-[(2-hydroxy-6-methyl-4-oxopyran-3-yl)-(4-methoxyphenyl)methyl]-6-methylpyran-4-one；4-hydroxy-3-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)-(4-methoxyphenyl)methyl]-6-methylpyran-2-one
• CAS: 82420-03-9
• 化学式: C₂₀H₁₈O₇
• 分子量: 370.359
• InChiKey: SKBKYSWCKDUCNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3'-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one) 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.33h， 以52%的产率得到3,3'-(4-methoxyphenylmethylene)bis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]
  参考文献：
  名称：

  Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction

  摘要：

  One-pot process was studied between a substituted 4-hydroxy-2H-pyran-2-one and aromatic aldehydes and ammonium acetate in the conditions of modified Hantzsch reaction in acid environment under thermal and microwave activation. Arylmethylenebis-4-hydroxy-2H-pyridin-2-ones, hydrochromenopyridinone, and their oxygen-containing heteroanalogs were isolated. A primary condensation was confirmed into bispyran-2-one adducts, and at the use of salicilaldehyde, into pyranochromene with subsequent recyclization of pyranone fragments in pyridinone ones.

  DOI：

  10.1134/s1070428018080092
• 作为产物：
  描述：

  3-乙基-4-羟基-6-甲基-2H-吡喃-2-酮 、 4-甲氧基苄醇 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以60%的产率得到3,3'-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)
  参考文献：
  名称：

  Iridium catalyzed acceptor-less dehydrogenative coupling of alcohols and 4-hydroxy-6-methyl-2-pyrone under microwave conditions

  摘要：

  Iridium catalyzed acceptor-less dehydrogenative coupling of benzyl type alcohols and 4-hydroxy-6-methyl-2-pyrone under microwave conditions afforded 3,3'-(arylmethylene)bis(4-hydroxy-6-methyl-2H-pyran-2-ones) in good yields. Crown Copyright (C) 2015 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.034

文献信息

• Synthesis of Methylenebis(4-hydroxy-2-pyrone) or Methylenebis(4-hydroxycoumarin) Derivatives by Organic Solid State Reaction
  作者：Hisahiro Hagiwara、Norikazu Fujimoto、Toshio Suzuki、Masayoshi Ando

  DOI：10.3987/com-99-8817

  日期：——

  formaldehyde under basic condition. Similarly, the electrochemical oxidation and the treatment of 6 under Knoevenagel reaction conditions are the other alternative procedure described for the preparation of these bis compounds. However, the first method lacks generality as it involves aqueous reaction media and the second procedure is useful to obtain only the methylene bridged bispyrone derivatives

  亚甲基桥连双香豆素，即双香豆素 (1) 和香豆素 (2)，除了保留其作为生化试剂的作用外，还可用作治疗血栓栓塞性疾病的口服抗凝剂。一些文献先例确实提供了合成这些化合物的方法，例如，亚甲基双(4-羟基-2-香豆素)衍生物(5)是通过4羟基香豆素(3)与甲醛水溶液在碱性条件下缩合制备的。类似地，电化学氧化和在 Knoevenagel 反应条件下对 6 的处理是用于制备这些双化合物的另一种替代方法。然而，第一种方法缺乏通用性，因为它涉及水性反应介质，而第二种方法仅适用于获得亚甲基桥接的双吡喃酮衍生物 (11a)。
• Application of biological-based nano and nano magnetic catalysts in the preparation of arylbispyranylmethanes
  作者：Mohammad Ali Zolfigol、Monireh Navazeni、Meysam Yarie、Roya Ayazi-Nasrabadi

  DOI：10.1039/c6ra18719f

  日期：——

  Herein, the utilization of 2-carbamoylhydrazine-1-sulfonic acid, carbamoylsulfamic acid and their related nano magnetic core–shell catalysts were described as biological-based nano catalysts with a urea moiety in the synthesis of arylbispyranylmethane derivatives under mild and eco-friendly reaction conditions. A good range of aromatic aldehydes were treated with 4-hydroxy-6-methyl-2-pyrone to give

  在本文中，2-氨基甲酰基肼-1-磺酸，氨基甲酰基氨基磺酸及其相关的纳米磁性核-壳催化剂的利用被描述为在温和且生态友好的反应下合成芳基双吡喃甲烷衍生物的具有脲部分的生物基纳米催化剂。条件。通过串联Knoevenagel缩合反应和Michael加成反应，在相对较短的反应时间内以高收率，用4-羟基-6-甲基-2-吡喃酮处理了一系列芳香醛，得到芳基双吡喃基甲烷衍生物。所提出的方案具有环保性质，高效率，简单的操作程序和良性反应条件的优点。
• Synthesis of N-formylmaleamic acid and some related N-formylamides
  作者：Edward J. Behrman、Edward L. Hillenbrand

  DOI：10.3184/030823408x304005

  日期：2008.3

  Two syntheses of N-formylmaleamic acid and some related N-formylamides are described which take place under very mild conditions.

  描述了在非常温和的条件下进行的 N-甲酰基马来酰胺酸和一些相关的 N-甲酰基酰胺的两种合成。
• Application of Fe₃O₄@SiO₂/(CH₂)₃-[imidazolium-SO₃H]Cl as a robust, magnetically recoverable solid acid catalyst for the facile preparation of arylbispyranylmethanes
  作者：Mohammad Ali Zolfigol、Mahdiyeh Navazeni、Meysam Yarie、Roya Ayazi-Nasrabadi

  DOI：10.1139/cjc-2017-0232

  日期：2017.12

  In this study, Fe₃O₄@SiO₂/(CH₂)₃-[imidazolium-SO₃H]Cl shows robust promoting capability in the synthesis of arylbispyranylmethane derivatives under mild and green conditions. Arylbispyranylmethanes were synthesized via efficient three-component reaction of various aromatic aldehydes with 4-hydroxy-6-methyl-2H-pyran-2-one. The nanomagnetic core-shell catalyst presented effective potential of at least eight times recycling applicability in the described synthetic procedure.

  在这项研究中，Fe3O4@SiO2/(CH2)3-[imidazolium-SO3H]Cl在温和和环保条件下表现出强大的促进能力，用于合成芳基双吡喃甲烷衍生物。芳基双吡喃甲烷通过各种芳香醛与4-羟基-6-甲基-2H-吡喃-2-酮的高效三组分反应合成。纳米磁性核壳催化剂在所描述的合成过程中展现出至少八次循环再利用的有效潜力。
• Anion functionalized ionic liquid from artificial sugar: a sustainable pathway for diverse bis-enol derivatives
  作者：Himani Sharma、Suman Srivastava

  DOI：10.1039/c9nj01899a

  日期：——

  An artificial sugar saccharine based anion-functionalized ionic liquid [Bmim]Sac was synthesized and used for new and straightforward strategies for the construction of a diverse range of bis-enols.

  一种基于人造糖精的阴离子功能化离子液体[Bmim]Sac被合成并用于构建多种双烯醇的新颖和简单策略。