methyl 2-(3-hydroxybenzyl)-3-oxobutanoate | 851181-63-0

• 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-(3-hydroxybenzyl)-3-oxobutanoate
• 英文别名: 2-(3-hydroxy-benzyl)-3-oxo-butyric acid methyl ester；methyl 2-[(3-hydroxyphenyl)methyl]-3-oxobutanoate
• CAS: 851181-63-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DMUOGYCUUQVHDC-UHFFFAOYSA-N

物化性质

• 沸点：
  354.2±27.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(3-hydroxybenzyl)-3-oxobutanoate 、 2-溴-1-甲基-1H-苯并咪唑 在 吡啶 、 铜 、 potassium carbonate 作用下， 反应 24.0h， 以20%的产率得到methyl 2-{3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzyl}-3-oxobutanoate
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461
• 作为产物：
  描述：

  methyl 2-(3-methoxybenzylidene)-3-oxobutanoate 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 45.0h， 生成 methyl 2-(3-hydroxybenzyl)-3-oxobutanoate
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461

文献信息

• DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF AS HIF ACTIVATORS
  申请人：ALTENBURGER Jean-Michel

  公开号：US20110294788A1

  公开（公告）日：2011-12-01

  The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.

  本发明涉及新型取代二氢吡唑酮衍生物，其制备以及作为转录因子HIF激活剂的治疗用途。
• [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。
• Derivatives of 2-pyridin-2-yl-pyrazol-3(2H)-one, preparation and therapeutic use thereof as HIF activators
  申请人：Altenburger Jean-Michel

  公开号：US08541455B2

  公开（公告）日：2013-09-24

  The present invention relates to novel substituted dihydropyrazolone derivatives, to their preparation and to their therapeutic use as activators of the transcription factor HIF.

  本发明涉及新型取代二氢吡唑酮衍生物，其制备方法及其作为转录因子HIF的激活剂的治疗用途。
• WATER STABILIZED MEDICINAL AEROSOL FORMULATION RELATED APPLICATIONS
  申请人：Kos Life Sciences, Inc.

  公开号：EP1569617A1

  公开（公告）日：2005-09-07
• DERIVES DE 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE COMME ACTIVATEURS DE HIF
  申请人：SANOFI

  公开号：EP2382205A2

  公开（公告）日：2011-11-02