2-hydroxy-2-methylbenzofuran-3(2H)-one | 33562-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-hydroxy-2-methylbenzofuran-3(2H)-one
• 英文别名: 2-Hydroxy-2-methyl-1-benzofuran-3-one
• CAS: 33562-07-1
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: BLAXAXFZKCAFQW-UHFFFAOYSA-N

物化性质

• 沸点：
  312.0±42.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对二甲苯 、 2-hydroxy-2-methylbenzofuran-3(2H)-one 在 三氟甲磺酸 作用下， 反应 0.17h， 以98%的产率得到2-(2,5-dimethylphenyl)-2-methylbenzofuran-3(2H)-one
  参考文献：
  名称：

  Iodine(III)-Mediated Tandem Acetoxylation−Cyclization of o-Acyl Phenols for the Facile Construction of α-Acetoxy Benzofuranones

  摘要：

  An efficient tandem acetoxylation-cyclization of o-acylphenols mediated by the combination of iodobenzene diacetate with tetrabutylammonium iodide provides a new convenient and useful route to alpha-acetoxy benzofuranones.

  DOI：

  10.1021/ol902067x
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.42h， 生成 2-hydroxy-2-methylbenzofuran-3(2H)-one
  参考文献：
  名称：

  使用丙炔进行 Sonogashira 反应的简便程序

  摘要：

  在 –78 °C 至室温下，仅在 THF 中使用两当量的丙炔即可实现芳基碘化物和丙炔的改性 Sonogashira 偶联。

  DOI：

  10.1055/a-1648-7074

文献信息

• 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.
• Dimethyldioxirane epoxidation of alkenes bearing two electron donating substituents.
  作者：Waldemar Adam、Lazaros Hadjarapoglou、Xiaoheng Wang

  DOI：10.1016/s0040-4039(00)79649-3

  日期：1991.3

  Various enol-type alkenes, such as 2,3-dimethylbenzodioxin (1), O-tetrabenzyl glycal (3), 1,2-bis(trimethylsilyloxy)cycloalkenes (9) were transformed in excellent yields to their labile epoxides by dimethyldioxirane (as acetone solution); the silyl ketene acetal 5 and 2-methyl-3-trimethylsilyloxybenzo[b]furan (7) gave the corresponding epoxide rearrangement products.
• A Convenient Procedure for Sonogashira Reactions Using Propyne
  作者：George A. Kraus、Joshua L. Alterman

  DOI：10.1055/a-1648-7074

  日期：2022.2

  A modified Sonogashira coupling of aryl iodides and propyne­ was achieved using only two equivalents of propyne in THF from –78 °C to room temperature.

  在 –78 °C 至室温下，仅在 THF 中使用两当量的丙炔即可实现芳基碘化物和丙炔的改性 Sonogashira 偶联。
• Iodine(III)-Mediated Tandem Acetoxylation−Cyclization of <i>o</i>-Acyl Phenols for the Facile Construction of α-Acetoxy Benzofuranones
  作者：Renhua Fan、Yi Sun、Yang Ye

  DOI：10.1021/ol902067x

  日期：2009.11.19

  An efficient tandem acetoxylation-cyclization of o-acylphenols mediated by the combination of iodobenzene diacetate with tetrabutylammonium iodide provides a new convenient and useful route to alpha-acetoxy benzofuranones.