3,3'-benzylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone] | 51424-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,3'-benzylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]
• 英文别名: 3,3'-(phenylmethylene)bis[4-hydroxy-6-methylpyridin-2(1H)-one]；3,3'-(benzylidene)bis[4-hydroxy-6-methylpyridin-2(1H)-one]；4,4'-dihydroxy-6,6'-dimethyl-1H,1'H-3,3'-phenylmethanediyl-bis-pyridin-2-one；3,3'-(phenylmethylene)bis(4-hydroxy-6-methylpyridin-2(1H)-one)；4-hydroxy-3-[(4-hydroxy-6-methyl-2-oxo-1H-pyridin-3-yl)-phenylmethyl]-6-methyl-1H-pyridin-2-one
• CAS: 51424-04-5
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: UNAMVXWYDIIHQX-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  633.6±55.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3'-(phenylmethylene)bis(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68%的产率得到3,3'-benzylidenebis[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

文献信息

• Synthesis of Functionalized 4<i>H</i>-Pyrano[3,2-<i>c</i>]pyridines from 4-Hydroxy-6-methyl-2-pyridone and Their Reactions. Unexpected New Routes to 3,3′-Benzylidenebis[4-hydroxy-6-methyl-2(1<i>H</i>)-3-pyridinone]s
  作者：Ramadan Ahmed Mekheimer、Nabil Helmi Mohamed、Kamal Usef Sadek

  DOI：10.1246/bcsj.70.1625

  日期：1997.7

  The reaction of 4-hydroxy-6-methyl-2-pyridone 1 with benzylidenemalononitriles in an ethanolic solution containing a catalytic amount of piperidine and α-cyanoacrylic esters in pyridine affords the corresponding 4H-pyrano[3,2-c]pyridines. However, it’s reaction with 3-(cyanomethylene)-2-indolinones gives either 2-amino-3-quinolinecarbonitriles or ethyl 2-amino-5′,6′-dihydro-7′-methyl-2,5′-dioxospiro-[indoline-3,4′-[4H]-pyrano[3,2-c]pyridine-3′-carboxylate. In contrast, the reaction of 1 with 3-aryl-2-cyano-2-propenethioamides affords 3,3′-benzylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]s. The reaction of the obtained 4H-pyrano[3,2-c]pyridines with acetic anhydride affords the corresponding fused system.

  4- 羟基-6-甲基-2-吡啶酮 1 与苯亚甲基丙二腈在含有一定量哌啶和 α-氰基丙烯酸酯催化剂的吡啶乙醇溶液中反应，生成相应的 4H-吡喃并[3,2-c]吡啶。然而，它与 3-（氰基亚甲基）-2-吲哚啉酮反应会生成 2-氨基-3-喹啉甲腈或 2-氨基-5′,6′-二氢-7′-甲基-2,5′-二氧杂螺-[吲哚啉-3,4′-[4H]-吡喃并[3,2-c]吡啶-3′-羧酸乙酯。与此相反，1 与 3-芳基-2-氰基-2-丙烯硫酰胺反应生成 3,3′-亚苄基双[4-羟基-6-甲基-2(1H)-3-吡啶酮]。将得到的 4H-吡喃并[3,2-c]吡啶与乙酸酐反应，可得到相应的融合体系。
• Synthesis and Phytotoxic Activity of New Pyridones Derived from 4-Hydroxy-6-Methylpyridin-2(1H)-one
  作者：Antonio Jacinto Demuner、Vania Maria Moreira Valente、Luiz Cláudio Almeida Barbosa、Akshat Rathi、Timothy Donohoe、Amber Thompson

  DOI：10.3390/molecules14124973

  日期：——

  Commercial dehydroacetic acid was converted into 4-hydroxy-6-methylpyridin-2(1H)-one (3), which was then condensed with several aliphatic aldehydes to produce seven new title compounds in variable yields (35–92%). Reaction of 3 with α,β-unsaturated aldehydes resulted in the formation of condensed pyran derivatives 4g’ and 4h’. A mechanism is proposed to explain the formation of such compounds. The

  商业脱氢乙酸被转化为 4-羟基-6-甲基吡啶-2(1H)-一 (3)，然后与几种脂肪醛缩合，以不同的产率 (35-92%) 产生七种新的标题化合物。3 与 α,β-不饱和醛的反应导致缩合吡喃衍生物 4g' 和 4h' 的形成。提出了一种机制来解释这些化合物的形成。评估了所有methylpyridin-2(1H)-one 衍生物对双子叶植物Ipomoea grandifolia 和Cucumis sativus 以及单子叶植物Sorghum bicolor 发育的影响。在 6.7 × 10-8 mol ai/g 底物的剂量下，这些化合物表现出一定的植物毒性选择性，对双子叶植物更具活性。这些化合物可用作开发更具活性的植物毒性产品的先导结构。
• A green and efficient synthesis of 3,3′-arylidenebis[4-hydroxy-6-methyl-2(1<i>H</i>)-3-pyridinone]s in water under microwave irradiation
  作者：Feng Shi、Longji Cao、Ning Ma、Ge Zhang、Rongshun Chen、Yajie Zhang、Shujiang Tu

  DOI：10.1002/jhet.210

  日期：——

  A series of 3,3′-arylidenebis[4-hydroxy-6-methyl-2(1H)-3-pyridinone]s were synthesized via three-component reactions of aromatic aldehydes, 4-hydroxy-6-methyl-2H-pyran-2-one, and ammonium acetate in water under microwave irradiation. This method has the advantages of environmental friendliness, short reaction time, high yields, and easy operation. This efficient synthesis not only offers an economical

  通过芳族醛的三组分反应合成了一系列3,3'-亚芳基双[4-羟基-6-甲基-2（1 H）-3-吡啶酮] s，4-羟基-6-甲基-2 H-吡喃-2-酮和微波辐射下的水中乙酸铵。该方法具有环境友好，反应时间短，收率高，操作简便的优点。这种有效的合成方法不仅为这类重要化合物提供了一种经济，绿色的合成策略，而且丰富了水中微波辅助合成方法的研究。J.杂环化​​学。（2010）。
• FINDLAY J. A.; KREPINSKY J.; SHUM F. Y.; TAM W. H. J., CAN. J. CHEM. <CJCH-AG>, 1976, 54, NO 2, 270-274
  作者：FINDLAY J. A.、 KREPINSKY J.、 SHUM F. Y.、 TAM W. H. J.

  DOI：——

  日期：——
• Synthesis of Fused 2Н-Pyridin-2-ones under the Conditions of Multicomponent Hantzsch Reaction
  作者：I. V. Strashilina、E. M. Arzyamova、O. V. Fedotova

  DOI：10.1134/s1070428018080092

  日期：2018.8

  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.