methyl 2-[(4-hydroxyphenyl)methyl]-3-oxopentanoate | 361576-47-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2-[(4-hydroxyphenyl)methyl]-3-oxopentanoate
• 英文别名: 2-(4-hydroxy-benzyl)-3-oxo-pentanoic acid methyl ester；Methyl 2-(4-hydroxyphenyl)methyl-3-oxopentanoate
• CAS: 361576-47-8
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: IVQQRFXHVAEJQS-UHFFFAOYSA-N

物化性质

• 沸点：
  366.0±27.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-[(4-hydroxyphenyl)methyl]-3-oxopentanoate 在 sodium acetate 、 caesium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 3-ethoxyimino-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyl}-pentanoic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of oxime ethers of α-acyl-β-phenylpropanoic acids as PPAR dual agonists

  摘要：

  Oxime ethers of alpha-acyl-(3-phenylpropanoic acids were prepared to apply as PPAR alpha and gamma dual agonists. Among them, compound 111 proved to exhibit potent in vitro activities with EC50 of 19 and 13 nM in PPAR alpha and gamma, respectively. It showed better glucose lowering effects than rosiglitazone 1 and ameliorated the lipid profile like plasma triglyceride in dbldb mice model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.050
• 作为产物：
  描述：

  3-氧代戊酸甲酯 在 哌啶 、 palladium dihydroxide 、 溶剂黄146 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 生成 methyl 2-[(4-hydroxyphenyl)methyl]-3-oxopentanoate
  参考文献：
  名称：

  Design and synthesis of oxime ethers of α-acyl-β-phenylpropanoic acids as PPAR dual agonists

  摘要：

  Oxime ethers of alpha-acyl-(3-phenylpropanoic acids were prepared to apply as PPAR alpha and gamma dual agonists. Among them, compound 111 proved to exhibit potent in vitro activities with EC50 of 19 and 13 nM in PPAR alpha and gamma, respectively. It showed better glucose lowering effects than rosiglitazone 1 and ameliorated the lipid profile like plasma triglyceride in dbldb mice model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.050

文献信息

• [EN] NOVEL COMPOUNDS AS AGONIST FOR PPAR GAMMA AND PPAR ALPHA, METHOD FOR PREPARATION OF THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAUX COMPOSES AGONISTES DE PPAR DOLLAR G(G) ET PPAR DOLLAR G(A), LEUR METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE LES CONTENANT
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2005040127A1

  公开（公告）日：2005-05-06

  The present invention relates to novel compounds accelerating the activity of Peroxisome proliferator-activated receptor gamma (PPARϜ) and alpha (PPARα), processes of preparing the same, and pharmaceutical compositions containing the same as an active agent.

  本发明涉及一种新型化合物，可加速过氧化物酶体增殖物激活受体γ（PPARϜ）和α（PPARα）的活性，以及制备这种化合物的方法，以及含有该化合物作为活性成分的药物组合物。
• Quinoline derivatives and medicinal use thereof
  申请人：——

  公开号：US20030212100A1

  公开（公告）日：2003-11-13

  A quinoline derivative represented by the following formula (1): 1 allows PPAR&agr; or &ggr; which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPAR&agr; or &ggr;.

  由以下式（1）表示的喹啉衍生物，可以使作为细胞核转录因子的PPAR&agr;或&ggr;功能强大且毒性低。通过使用这种化合物作为活性成分，可以提供与PPAR&agr;或&ggr;相关的各种疾病的预防或治疗剂。
• QUINOLINE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1266888A1

  公开（公告）日：2002-12-18

  A quinoline derivative represented by the following formula (1): allows PPARα or γ which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPARα or γ.

  由下式（1）代表的喹啉衍生物： 可使作为核内转录因子的 PPARα 或 γ 发挥强大的功能，且毒性低。使用这种化合物作为活性成分，可以提供一种预防或治疗与 PPARα 或 γ 有关的各种疾病的药物。
• Morita–Baylis–Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI–MS(/MS)
  作者：Rosimeire C. Barcelos、Lucas A. Zeoly、Manoel T. Rodrigues、Bruno R. V. Ferreira、Marcos N. Eberlin、Fernando Coelho

  DOI：10.1007/s00706-015-1427-6

  日期：2015.9

  We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring.