4-hydroxy-3-((4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl)-6-methyl-2H-pyran-2-one | 60045-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-3-((4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl)-6-methyl-2H-pyran-2-one
• 英文别名: Bis-<4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl>methane；3,3′-methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)；4,4'-dihydroxy-6,6'-dimethyl-3,3'-methanediyl-bis-pyran-2-one；Bis-3,3'-<4-hydroxy-6-methyl-pyron-2>-methan；4,4'-Dihydroxy-6,6'-dimethyl-3,3'-methylen-di-pyr-2-on；3,3'-Methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)；4-hydroxy-3-[(4-hydroxy-6-methyl-2-oxopyran-3-yl)methyl]-6-methylpyran-2-one
• CAS: 60045-30-9
• 化学式: C₁₃H₁₂O₆
• 分子量: 264.235
• InChiKey: DVLLGHPCJPEUHA-UHFFFAOYSA-N

物化性质

• 熔点：
  245-500 °C
• 沸点：
  464.7±45.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-((4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl)-6-methyl-2H-pyran-2-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 17.0h， 以73%的产率得到3,7-dimethyl-1H,9H,10H-dipyrano<4,3-b:3',4'-e>pyran-1,9-dione
  参考文献：
  名称：

  Moreno-Manas, Marcial; Ribas, Jordi; Virgili, Albert, Synthesis, 1985, # 6/7, p. 699 - 701

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 N,N,N',N'-四甲基对苯二胺 以 aq. phosphate buffer 、 乙醇 为溶剂， 以80%的产率得到4-hydroxy-3-((4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methyl)-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Electrochemically induced cross-dehydrogenative coupling (CDC) reaction. An efficient electrochemical method for the synthesis of dicoumarols

  摘要：

  电化学合成双香豆素是通过电化学氧化N,N,N′,N′-四甲基-1,4-苯二胺在4-羟基香豆素衍生物存在下进行的。

  DOI：

  10.1039/c4ra08181a

文献信息

• Anodic oxidation of pyrones and coumarins.
  作者：ATSUKO NISHIYAMA、HIDEO ETO、MASANOBU IGUCHI、SHOSUKE YAMAMURA

  DOI：10.1248/cpb.31.2853

  日期：——

  Triacetic lactone, 4-hydroxycoumarins and 2-chloromethyl-5-hydroxy-4-pyrone were subjected to anodic oxidation in methanol containing LiClO4 or NaCN to afford the corresponding methoxy or cyano compounds. In basic media, however, bispyrone and biscoumarol were produced from triacetic lactone (4-hydroxy-6-methyl-2-pyrone) and 4-hydroxycoumarin, respectively. The formation processes of these oxidation products are discussed.

  三甲基内酯、4-羟基香豆素和2-氯甲基-5-羟基-4-吡喃酮在含LiClO4或NaCN的甲醇中进行阳极氧化,分别得到相应的甲氧基或氰基化合物。但在碱性介质中,三甲基内酯和4-羟基香豆素分别生成联吡喃酮和联香豆素。并对这些氧化产物的形成过程进行了讨论。
• ANODIC OXIDATION OF PYRONES AND RELATED COMPOUNDS
  作者：Masanobu Iguchi、Atsuko Nishiyama、Hideo Eto、Shosuke Yamamura

  DOI：10.1246/cl.1980.1323

  日期：1980.10.5

  Triacetic lactone, 4-hydroxycoumarins, and kojic acid derivative were subjected to anodic oxidation in MeOH containing LiClO4 or NaCN to afford the corresponding methoxy or cyano compounds. In a basic media, however, dipyrone and dicoumarol were produced from triacetic lactone and 4-hydroxycoumarin, respectively. The formation process of 3-methoxytriacetic lactone as well as of 3-cyanotriacetic lactone

  三乙酸内酯、4-羟基香豆素和曲酸衍生物在含有 LiClO4 或 NaCN 的 MeOH 中进行阳极氧化，得到相应的甲氧基或氰基化合物。然而，在碱性培养基中，双吡喃酮和双香豆素分别由三乙酸内酯和 4-羟基香豆素产生。还介绍了 3-甲氧基三乙酸内酯和 3-氰基三乙酸内酯的形成过程。
• 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)。
• A Multicomponent Carba-Betti Strategy to Alkylidene Heterodimers - Total Synthesis and Structure-Activity Relationships of Arzanol
  作者：Alberto Minassi、Lavinia Cicione、Andreas Koeberle、Julia Bauer、Stefan Laufer、Oliver Werz、Giovanni Appendino

  DOI：10.1002/ejoc.201101193

  日期：2012.2

  Using the synthesis of the heterodimeric phloroglucinyl pyrone arzanol as a benchmark reaction, a carba-version of the Betti multicomponent reaction has been developed. Capitalizing on the fluorous activation of the phenolic component and the use of iminium ions as bivalent and "transmissive" aldehyde equivalents, the reaction has been used to colonize a biologically privileged but previously inaccessible

  使用异二聚体间苯二酚吡喃酮 arzanol 的合成作为基准反应，已经开发了 Betti 多组分反应的 carba 版本。利用酚类成分的氟活化和亚胺离子作为二价和“传递性”醛等价物的使用，该反应已被用于殖民一个生物学上特权但以前无法进入的化学空间区域，并研究 arzanol 的结构 - 活性关系针对一系列促炎靶点（mPGES-1、5-LO）。
• Et2AlCl Promoted Coupling Reactions of 4-Hydroxy-2-pyrone or 4-Hydroxycoumarine with Aldehydes: Synthesis of Methylenebis-(4-hydroxy-2-pyrone) or Methylenebis-(4-hydroxycoumarine) Derivatives
  作者：Hisahiro Hagiwara、Shigeki Miya、Toshio Suzuki、Masayoshi Ando、Isao Yamamoto、Michiharu Kato

  DOI：10.3987/com-98-8429

  日期：——

  Methylenebis(4-hydroxy-2-pyrone) or methylenebis(4-hydroxy-coumarine) derivatives (5) have been synthesized from 4-hydroxy-2-pyrones (6) and (8) or 4-hydroxycoumarine (10) with aldehydes (4) in the presence of diethylaluminum chloride.