methyl 2-(2-hydroxyphenyl)-2-oxo-acetate | 34073-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(2-hydroxyphenyl)-2-oxo-acetate
• 英文别名: Methyl o-hydroxyphenylglyoxylate；methyl 2-hydroxyphenylglyoxylate；2-hydroxy-α-oxo-benzeneacetic acid, methyl ester；Benzeneacetic acid, 2-hydroxy-alpha-oxo-, methyl ester；methyl 2-(2-hydroxyphenyl)-2-oxoacetate
• CAS: 34073-46-6
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: YXZAANSFGURKCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-hydroxyphenyl)-2-oxo-acetate 在 甲酸 、 氯磺酰异氰酸酯 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 生成 methyl benzo[e][1,2,3]oxathiazine-4-carboxylate 2,2-dioxide
  参考文献：
  名称：

  Ni催化的不对称氢化反应合成手性α-取代α-氨基酸和胺衍生物。

  摘要：

  首次成功开发了高效的Ni催化的环状N-磺酰基酮亚胺基酯的不对称加氢反应，提供了各种具有优异效果的手性α-单取代α-氨基酸衍生物（97-99％的收率，90至> 99％ ee）。环状N-磺酰基酮亚胺也被充分氢化，以98-99％的收率和97至＞ 99％的ee得到手性胺衍生物。仅使用0.2mol％的催化剂，克级不对称氢化进行得很好，产率为85％，ee为99％。

  DOI：

  10.1039/d0cc01220c
• 作为产物：
  描述：

  2-(2-环己酮)-2-羟基乙酸甲酯 在 碘酸 作用下， 以 二甲基亚砜 、 环己烯 为溶剂， 反应 12.0h， 以65%的产率得到methyl 2-(2-hydroxyphenyl)-2-oxo-acetate
  参考文献：
  名称：

  一种2-(2-羟基苯基)-2-氧乙酸酯的合成方法

  摘要：

  本发明公开了一种2‑(2‑羟基苯基)‑2‑氧乙酸酯的合成方法，该方法是以环己酮和乙醛酸酯为原料，室温下经催化进行Aldol缩合反应，制得中间体2‑羟基‑2‑(2'‑氧环己基)乙酸酯，再通过碘酸‑二甲基亚砜进行氧化与脱氢芳构化反应，得到2‑(2‑羟基苯基)‑2‑氧乙酸酯。本发明2‑(2‑羟基苯基)‑2‑氧乙酸酯的合成方法，首次用碘酸进行脱氢芳构化的反应，实现一步进行氧化和芳构化的过程，该方法所用试剂均廉价易得，反应条件温和，容易操控，反应后处理简单，较适用于2‑(2‑羟基苯基)‑2‑氧乙酸酯等同类产品的规模制备。

  公开号：

  CN104710305B

文献信息

• Methods for producing 2-(2-hydroxyphenyl)-2-(alkoxyimino)-N-methylacetamide derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US06700017B1

  公开（公告）日：2004-03-02

  The present invention provides processes for preparing 2-(2-hydroxyphenyl)-2-(alkoxyimino)-N-methylacetamides, to intermediates for this preparation, and to processes for preparing those intermediates.

  本发明提供了制备2-(2-羟基苯基)-2-(烷氧基亚胺)-N-甲基乙酰胺的工艺，以及用于制备这些中间体的中间体，以及制备这些中间体的工艺。
• Method of producing methoxyimino acetic amide
  申请人：Bayer Aktiengesellschaft

  公开号：US06660872B1

  公开（公告）日：2003-12-09

  The present invention relates to novel processes for preparing methoxyimino-acetamides.

  本发明涉及制备甲氧基亚胺基乙酰胺的新工艺。
• ω-Oxygenated prenylated coumarins from Ferula communis
  作者：Giovanni Appendino、Silvia Tagliapietra、Pierluigi Gariboldi、Gian Mario Nano、Vincenzo Picci

  DOI：10.1016/0031-9422(88)80778-7

  日期：1988.1

  Abstract From the toxic variety of Ferula communis, derivatives of the prenylated coumarins ferulenol and ferprenin bearing an oxygen function (hydroxyl, acetoxyl, aldehydic carbonyl) at the ω-composition have been isolated. The structures of the coumarins were established by spectral methods and by chemical reactions. Photooxygenation of ferulenol and (E) ω-hydroxyferulenol gave o-hydroxyphenylglyoxylic

  摘要 从有毒的 Ferula community 中分离出异戊二烯化香豆素阿魏醇和 ferprenin 的衍生物，它们在 ω 组成上带有氧官能团（羟基、乙酰氧基、醛羰基）。香豆素的结构是通过光谱方法和化学反应确定的。阿魏醇和 (E) ω-羟基阿魏醇的光氧化产生邻羟基苯基乙醛酸酯，这是由于 4-羟基香豆素核的氧化脱羰和异戊二烯侧链的丢失。也从植物提取物中分离出邻羟基苯基乙醛酸乙酯，表明这种类型的反应可能是导致植物样品和 Ferula community 提取物中异戊二烯化香豆素降解的原因。
• Lewis Base-Catalyzed Intramolecular Vinylogous Aldol Reaction and Chemoselective Syntheses of 3-Hydroxy-2,3-Disubstituted Dihydrobenzofurans and Indolines
  作者：Jiayong Zhang、Zhengjie He

  DOI：10.1021/acs.joc.3c01313

  日期：2023.9.15

  A Lewis base-catalyzed intramolecular vinylogous aldol reaction of o-(allyloxy)phenyl ketoesters or o-(allylamino)phenyl ketoesters has been developed. This reaction provides ready access to 3-hydroxy-2,3-disubstituted dihydrobenzofurans and indolines in high yields with excellent chemoselectivity and diastereoselectivity. An acid-promoted dehydration of such products further extends the utility of

  开发了路易斯碱催化的邻-(烯丙氧基)苯基酮酯或邻-(烯丙氨基)苯基酮酯的分子内插烯羟醛反应。该反应可以以高产率轻松获得 3-羟基-2,3-二取代的二氢苯并呋喃和二氢吲哚，并具有优异的化学选择性和非对映选择性。此类产物的酸促进脱水进一步将该反应的用途扩展到2-烯基苯并呋喃和吲哚的合成。
• 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.