methyl 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylate | 117375-43-6

• 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: methyl 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylate
• 英文别名: Methyl 2-hydroxy-3-oxo-1-benzofuran-2-carboxylate
• CAS: 117375-43-6
• 化学式: C₁₀H₈O₅
• 分子量: 208.171
• InChiKey: FQRXKKTZMZKTQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  α-bromo-1,2-benzisoxazole-3-acetic acid methyl ester 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.5h， 生成 methyl 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylate
  参考文献：
  名称：

  Ueda, Shozo; Naruto, Shunsuke; Yoshida, Toyokichi, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1013 - 1022

  摘要：

  DOI：

文献信息

• Visible Light-Induced and Singlet Oxygen-Mediated Photochemical Conversion of 4-Hydroxy-α-benzopyrones to 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using Rose Bengal as a Photosensitizer
  作者：Goutam Brahmachari、Indrajit Karmakar

  DOI：10.1021/acs.joc.0c00726

  日期：2020.7.17

  protocol has been accomplished for the first time for the photochemical transformation of 4-hydroxy-α-benzopyrones to a new series of biorelevant 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides and 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates using rose bengal as a triplet photosensitizer at ambient temperature. Metal-free one-pot synthesis, broader substrate scope, good-to-excellent yields,

  首次完成了可见光诱导和单线态氧介导的绿色协议的开发，用于将4-羟基-α-苯并吡喃酮进行光化学转化为一系列新的生物相关的2-羟基-3-氧代-2,3。在室温下，使用玫瑰红作为三重态光敏剂，将-二氢苯并呋喃-2-羧酰胺和2-羟基-3-氧代-2,3-二氢苯并呋喃-2-羧酸酯。这种新开发的方法的主要特点是无金属一锅法合成，更广泛的底物范围，良好至优异的产率，使用经济高效且环保的原料和光敏剂以及能源效率。
• 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.
• UEDA, SHOZO;NARUTO, SHUNSUKE;YOSHIDA, TOYOKICHI;SAWAYAMA, TADAHIRO;UNO, H+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N 5, C. 1013-1021
  作者：UEDA, SHOZO、NARUTO, SHUNSUKE、YOSHIDA, TOYOKICHI、SAWAYAMA, TADAHIRO、UNO, H+

  DOI：——

  日期：——
• Ueda, Shozo; Naruto, Shunsuke; Yoshida, Toyokichi, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1013 - 1022
  作者：Ueda, Shozo、Naruto, Shunsuke、Yoshida, Toyokichi、Sawayama, Tadahiro、Uno, Hitoshi

  DOI：——

  日期：——