methyl 3-(4-methoxyphenyl)-2-oxopropanoate | 69882-69-5

• 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 3-(4-methoxyphenyl)-2-oxopropanoate
• 英文别名: 4-methoxyphenylpyruvic acid methyl ester；methyl 3-(4-methoxyphenyl)pyruvate；(4-methoxy-phenyl)-pyruvic acid methyl ester；(4-Methoxy-phenyl)-brenztraubensaeure-methylester
• CAS: 69882-69-5
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: YFKAHHRRSJDIOX-UHFFFAOYSA-N

物化性质

• 沸点：
  322.9±25.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)
• 保留指数：
  1521.4

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-methoxyphenyl)-2-oxopropanoate 在 氢氧化钾 、 乙醇 作用下， 生成 2-(4-methoxy-benzyl)-3-(4-methoxy-phenyl)-4,5-dioxo-tetrahydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Cagniant, Annales de Chimie (Cachan, France), 1952, vol. <12> 7, p. 442,464

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3-cyano-3-(p-methoxyphenyl)-pyruvate 在 硫酸 、 溶剂黄146 作用下， 生成 methyl 3-(4-methoxyphenyl)-2-oxopropanoate
  参考文献：
  名称：

  Cagniant, Annales de Chimie (Cachan, France), 1952, vol. <12> 7, p. 442,464

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of analogues of butyrolactone I and molecular model of its interaction with CDK2
  作者：Miguel F. Braña、M. Luisa García、Berta López、Beatriz de Pascual-Teresa、Ana Ramos、Jose M. Pozuelo、M. Teresa Domínguez

  DOI：10.1039/b403052d

  日期：——

  A series of analogues of butyrolactone I, a natural product isolated from Aspergillus terreus that selectively inhibits the CDK2 and CDK1 kinases and that has been found to exhibit an interesting antiproliferative activity, have been synthesized. Its antitumor activity has been tested. Molecular models of the complex between butyrolactone I and the CDK2 active site have been built using a combination of conformational search and automated docking techniques. The stability of the resulting complexes has been assessed by molecular dynamics simulations and the experimental results obtained for the synthesized analogues are rationalized based on the molecular models.

  一系列丁酯内酯I的类似物被合成，该天然产物是从土曲霉（Aspergillus terreus）中分离出来的，能够选择性抑制CDK2和CDK1激酶，并且已被发现表现出有趣的抗增殖活性。其抗肿瘤活性已被测试。通过结合构象搜索和自动对接技术构建了丁酯内酯I与CDK2活性位点之间复合物的分子模型。通过分子动态模拟评估了所得到复合物的稳定性，并基于分子模型对合成类似物获得的实验结果进行了合理化分析。
• Synthesis and aldose reductase-inhibitory activities of structural analogues of WF-3681, a novel aldose reductase inhibitor.
  作者：TAKAYUKI NAMIKI、YUKIHISA BABA、YASUTAKA SUZUKI、MOTOAKI NISHIKAWA、KOZO SAWADA、YOSHIKUNI ITOH、TERUO OKU、YOSHIHIKO KITAURA、MASASHI HASHIMOTO

  DOI：10.1248/cpb.36.1404

  日期：——

  Various analogues of WF-3681 (1a), a novel aldose reductase inhibitor, were synthesized and examined for aldose reductase-inhibitory activity. It was found that the carboxylic acid function is necessary and the side-chain length is important for the activity. Furthermore, the lipophilicities of the benzene ring and the enol ether group are significant for increasing the activity.

  合成了多种WF-3681（1a）的类似物，这是一种新型的醛糖还原酶抑制剂，并对其醛糖还原酶抑制活性进行了研究。结果发现，羧酸基团是必要的，侧链长度对活性也很重要。此外，苯环和烯醇醚基团的脂溶性对提高活性具有重要意义。
• Synthesis of Simple 3,4-Diarylpyrrole-2,5-dicarboxylic Acids and Lukianol A by Oxidative Condensation of 3-Arylpyruvic Acids with Ammonia
  作者：Wolfgang Steglich、Claudia Hinze、Andreas Kreipl、Andreas Terpin

  DOI：10.1055/s-2007-965876

  日期：2007.2

  Several derivatives of 3,4-diaryl- and 3,4-diindolylpyrrole-2,5-dicarboxylic acids including lycogalic acid A and two Halomonas­ metabolites were synthesized by oxidative dimerization of arylpyruvic acids or arylpyruvates in the presence of ammonia. The reaction can be applied for a short synthesis of lukianol A.

  在氨存在下，通过芳基丙酮酸或芳基丙酮酸盐的氧化二聚，合成了 3,4- 二芳基和 3,4- 二吲哚基吡咯-2,5-二羧酸的几种衍生物，其中包括lukogalic 酸 A 和两种 Halomonas 代谢物。该反应可用于苜蓿醇 A 的短期合成。
• Synthesis, stereochemistry and pharmacological activity of rac.-<i>cis</i>-tetrahydro-6-hydroxy-7-(4-methoxyphenyl)-1,4-thiazepin-5(2<i>H</i>)-ones
  作者：Erno Mohacsi、Jay P. O'Brien、Louis J. Todaro

  DOI：10.1002/jhet.5570290135

  日期：1992.1

  Reaction of 2-aminoethanethiol (3) with trans-3-(p-methoxyplienyl)glycidate (4) gave the rac.-cis-1,4-thiazepinone 5 and a by-product 6. The structure of 5 was proven by X-ray crystallography. The X-ray data revealed that this compound adopts the chair conformation in the solid state and the heterocyclic ring is sevenmembered. The structure of the by-product 6 was elucidated on the basis of spectral

  2-氨基乙硫醇（3）与反式-3-（对甲氧基吡啶基）缩水甘油酸酯（4）的反应给出了rac.-顺-1,4-噻嗪酮5和副产物6。X射线晶体学证明5的结构。X射线数据表明该化合物在固态下采用椅子构象，杂环为七元。根据光谱数据阐明了副产物6的结构。化合物9和10作为钙通道阻滞剂是无活性的。
• Process for production of phenyllactic acid derivative
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0696566A1

  公开（公告）日：1996-02-14

  A process for producing a phenyllactic acid derivative comprises hydrogenating a phenylpyruvic acid derivative in the presence of a catalyst containing at least one element selected from the Group VIII elements of the periodic table. The process provides a phenyllactic acid derivative useful as an intermediate in the production of pharmaceuticals and agricultural chemicals. The process uses as a starting material a phenylpyruvic acid derivative which is easily synthesized. The process is simpler in operation and provides a higher yield than conventional processes.

  生产苯乳酸衍生物的工艺包括在含有至少一种选自元素周期表第八族元素的催化剂存在下氢化苯丙酮酸衍生物。该工艺提供了一种苯基乳酸衍生物，可用作生产药品和农药的中间体。该工艺使用易于合成的苯丙酮酸衍生物作为起始原料。与传统工艺相比，该工艺操作简单，产率高。