methyl 2-hydroxy-4-oxo-4-phenylbutanoate | 352547-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-hydroxy-4-oxo-4-phenylbutanoate
• 英文别名: 2-hydroxy-4-oxo-4-phenyl-butyric acid methyl ester
• CAS: 352547-72-9
• 化学式: C₁₁H₁₂O₄
• mdl: MFCD30479298
• 分子量: 208.214
• InChiKey: SFOPLUFDXYYZJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  369.2±32.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 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-hydroxy-4-oxo-4-phenylbutanoate 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 4-Methoxycarbonyl-2-phenyl-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists

  摘要：

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00043-9
• 作为产物：
  描述：

  乙醛酸甲酯 、 苯乙酮 在 indium(III) chloride 作用下， 反应 120.0h， 以59%的产率得到methyl 2-hydroxy-4-oxo-4-phenylbutanoate
  参考文献：
  名称：

  InCl 3-乙醛酸一水合物和乙醛酸酯与各种酮的催化直接羟醛反应：范围和局限性

  摘要：

  各种酮与乙醛酸和乙醛酸酯的直接醛醇缩合反应以良好的产率和高的区域选择性提供了α-羟基酸和α-羟基酯。

  DOI：

  10.1016/s0040-4020(01)00309-x

文献信息

• ——
  作者：G. S. Posyagin、E. Yu. Posyagina、V. V. Zalesov、S. S. Kataev

  DOI：10.1023/a:1013950903524

  日期：——

  Polarographic reduction of methyl 4-aryl-2,4-dioxobutanoates in aqueous 2-propanol involves two cathodic waves and yields methyl 4-aryl-2,4-dihydroxybutanoates.
• InCl3-Catalyzed direct aldol reactions of glyoxylic acid monohydrate and glyoxylates with various ketones: scope and limitations
  作者：Teck-Peng Loh、Li-Chun Feng、Lin-Li Wei

  DOI：10.1016/s0040-4020(01)00309-x

  日期：2001.5

  The direct aldol reactions of various ketones with glyoxylic acid and glyoxylates afforded the α-hydroxy acid and α-hydroxy esters in good yields and high regioselectivities.

  各种酮与乙醛酸和乙醛酸酯的直接醛醇缩合反应以良好的产率和高的区域选择性提供了α-羟基酸和α-羟基酯。
• Replacement of the quinoline system in 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonists
  作者：G.A.M Giardina、M Artico、S Cavagnera、A Cerri、E Consolandi、S Gagliardi、D Graziani、M Grugni、D.W.P Hay、M.A Luttmann、R Mena、L.F Raveglia、R Rigolio、H.M Sarau、D.B Schmidt、G Zanoni、C Farina

  DOI：10.1016/s0014-827x(99)00043-9

  日期：1999.6

  Results from a medicinal chemistry approach aimed at replacing the quinoline ring system in the potent and selective human neurokinin-3 (hNK-3) receptor antagonists 1-4 of general formula I are discussed. The data give further insight upon the potential NK-3 pharmacophore. In particular, it is highlighted that both the benzene-condensed ring and the quinoline nitrogen are crucial determinants for optimal binding affinity to the hNK-3 receptor. Some novel compounds maintained part of the binding affinity to the receptor (5, 6, 10 and 13) and compound 5, featuring the naphthalene ring system, appears to be suitable for further modifications; it offers the option to introduce electron-withdrawing groups at position 2 and 4, conferring on the ring an overall electron-deficiency similar to that of the quinoline. (C) 1999 Elsevier Science S.A. All rights reserved.