4-羟基-3-甲氧基-2H-苯并吡喃-2-酮 | 37571-01-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-羟基-3-甲氧基-2H-苯并吡喃-2-酮
• 英文名称: 4-hydroxy-3-methoxycoumarin
• 英文别名: 3-Methoxy-4-hydroxycoumarin；4-hydroxy-3-methoxychromen-2-one
• CAS: 37571-01-0
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: ZAKGGCVXGNRZPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 4-羟基-3-甲氧基-2H-苯并吡喃-2-酮 在 乙醚 作用下， 生成 2,3-dimethoxy-chromen-4-one
  参考文献：
  名称：

  Arndt et al., Chemische Berichte, 1951, vol. 84, p. 333,340, 341,

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基香豆素 在 盐酸 、 sodium azide 、 sodium nitrite 作用下， 反应 5.25h， 生成 4-羟基-3-甲氧基-2H-苯并吡喃-2-酮
  参考文献：
  名称：

  Photoreactions of 4- and 3-Azidocoumarins in the Presence of Nucleophiles

  摘要：

  The photoreactions of 4-azidocoumarins (1) and 3-azidocoumarin (2) in the presence of nucleophiles such as alcohols, thiol or amines generally gave 4-substituted 3-amino- and/or 3-substituted 4-aminocoumarins, while pyrone ring fission with incorporation of two moles of nucleophile was observed in the reaction of 1 in the presence of primary or secondary aliphatic amine as a nucleophile. Plausible mechanisms for these reactions are suggested.

  DOI：

  10.3987/com-92-s(t)88

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。
• Reaction of Superoxide with Aci-Reductones
  作者：Aryeh A. Frimer、Vered Marks、Pessia Gilinsky-Sharon、Ladis Aljadeff、Hugo E. Gottlieb

  DOI：10.1021/jo00119a031

  日期：1995.7

  Three reductones, 2,3-dihydroxy-4,4-diphenyl-2,5-cyclohexadien-1-one(11), 3,4-dihydroxycoumarin (35), and 3,4-dihydroxyspiro[5.5]undecan-3-en-4-one (64), were prepared and subsequently reacted with superoxide anion radical(O-2(.-)), generated from KO2 and 18-crown-6 polyether. The reactions were carried out in aprotic media and quenched with methyl iodide which facilitates the trapping of the various oxyanions formed. While a plethora of products were formed in each case [2-hydroxy-2-methyl-4,4-diphenyl-5-cyclohexene-1,3-dione (17), dimethyl 4,4-diphenylglutaconate (18), methyl 4,4-diphenyl-3-butenoate (19), phenylcinnamaldehyde (20), methyl 3-phenylcinnamate (21), and benzophenone (22) from 11; 3-hydroxy-2-methoxycoumarin (39), 2-carbomethoxy-2-hydroxy-3-coumaranone (40), 2-hydroxy-2-methyl-3-coumaranone (41), methyl o-hydroxyphenylglyoxylate (42), methyl salicylate (43), and catechol (44) from 35; and 2,4-dihydroxyspiro[5.5]undeca-1,4-dien-3-one (66), 2-hydroxyspiro[4.5]dec-1-en-3-one (70), dimethyl 1,1-cyclohexanediacetate (73), and dimethyl alpha-keto-1-[(methoxycarbonyl)methyl]cyclohexane (75) from 64], an overall analysis of the product distribution indicates that the basic elements of the reaction sequence are the same. The first step involves facile deprotonation and the concomitant generation of the reductone monoanion, a process which lends support to the suggestion of Afanas'ev and co-workers (Afanas'ev, I. B.; Grabovetskii, V. V.; Kuprianova, N. S. J. Chem. Sec. Perkin Trans. 2 1987, 281-285). Oxidation of this monoanion yields the corresponding triketone. Of the various options available to this polyketone, superoxide attack at the most electrophilic central carbonyl followed by oxidative cleavage and/or benzylic acid rearrangement are clearly the most prominent. These are followed by a variety of base catalyzed autoxidative processes which are highly dependent on the nature of the substrate.
• Diruthenium(II,II) tetrakis(acetate) as a catalyst of choice for intermolecular insertion of stabilized diazocompounds into OH bonds
  作者：Sergio Cenini、Giancarlo Cravotto、Giovanni B Giovenzana、Giovanni Palmisano、Andrea Penoni、Stefano Tollari

  DOI：10.1016/s0040-4039(02)00618-4

  日期：2002.5

  In the presence of 3 mol% of [Ru(OAc)(2)](2) at 90degreesC in hexafluorobenzone or alcohols as solvents the highly stabilized diazocoumarin 1 undergoes insertion into the OH bond of alcohols (and phenols) regio- and chemoselectively, affording the corresponding 3-alkoxy-4-hydroxycoumarin in moderate to excellent yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• ANTHELMINTIC AND ANTICOCCIDAL 3-CARBAMOYL-4-HYDROXYCOUMARINS, METHOD OF USE AND COMPOSITIONS
  申请人：THE UPJOHN COMPANY

  公开号：EP0550493A1

  公开（公告）日：1993-07-14