methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate | 653578-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate
• 英文别名: (S)-Methyl 2-ethyl-5-hydroxy-2,3-dihydrobenzofuran-2-carboxylate；methyl (2S)-2-ethyl-5-hydroxy-3H-1-benzofuran-2-carboxylate
• CAS: 653578-63-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: DHUHQGBTOIJWNC-LBPRGKRZSA-N

物化性质

• 沸点：
  349.4±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate 在 氢氧化钾 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (S)-5-{3-[2-Chloro-4-(2,2,2-trifluoro-ethyl)-phenoxy]-propoxy}-2-ethyl-2,3-dihydro-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity

  摘要：

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.

  DOI：

  10.1021/jm050373g
• 作为产物：
  描述：

  (S)-2-Ethyl-2,3-dihydro-benzofuran-2-carboxylic acid 在 氢氧化钾 、 三氯化铝 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 生成 methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Novel 2,3-Dihydrobenzofuran-2-carboxylic Acids:  Highly Potent and Subtype-Selective PPARα Agonists with Potent Hypolipidemic Activity

  摘要：

  The design and synthesis of a novel class of 2,3-dihydrobenzofuran-2-carboxylic acids as highly potent and subtype-selective PPAR alpha agonists are reported. Systematic study of structure-activity relationships has identified several key structural elements within this class for maintaining the potency and subtype selectivity. Select compounds were evaluated in animal models of dyslipidemia using Syrian hamsters and male Beagle dogs, and all these compounds displayed excellent cholesterol- and triglyceride-lowering activity at dose levels that were much lower than the marketed weak PPAR alpha agonist fenofibrate.

  DOI：

  10.1021/jm050373g

文献信息

• Ppar alpha selective compounds for the treatment of dyslipidemia and other lipid disorders
  申请人：Shi Q. Guo

  公开号：US20050228044A1

  公开（公告）日：2005-10-13

  A class of benzodihydrofuran compounds having the structure of formula (I) below and pharmaceutically acceptable salts thereof are useful as therapeutic compounds, particularly in the treatment of hyperlipidemia, hypercholesterolemia, dyslipidemia, and other lipid disorders, and in delaying the onset of or reducing the risk of conditions and sequelae that are associated with these diseases, such as atherosclerosis.

  一类苯并二氢呋喃化合物，其结构式为（I），以及其药学上可接受的盐，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的病症和后遗症的发生风险，如动脉粥样硬化。
• Compounds for the Treatment of Dyslipidemia and Other Lipid Disorders
  申请人：Dropinski F. James

  公开号：US20080039514A1

  公开（公告）日：2008-02-14

  A class of compounds having Formula I and pharmaceutically acceptable salts thereof are useful as therapeutic compounds, particularly in the treatment of hyperlipidemia, hypercholesterolemia, dyslipidemia, and other lipid disorders, and in delaying the onset of or reducing the risk of developing conditions and sequelae that are associated with these diseases, such as atherosclerosis.

  具有I式和其药物可接受的盐的化合物类别，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的病症和后遗症的发生风险，例如动脉粥样硬化。
• PPAR alpha selective compounds for the treatment of dyslipidemia and other lipid disorders
  申请人：Merck & Co., Inc.

  公开号：US07524882B2

  公开（公告）日：2009-04-28

  A class of benzodihydrofuran compounds having the structure of formula (I) below and pharmaceutically acceptable salts thereof are useful as therapeutic compounds, particularly in the treatment of hyperlipidemia, hypercholesterolemia, dyslipidemia, and other lipid disorders, and in delaying the onset of or reducing the risk of conditions and sequelae that are associated with these diseases, such as atherosclerosis.

  一类苯并二氢呋喃化合物，其结构式（I）如下，以及其药学上可接受的盐，可用作治疗化合物，特别是用于治疗高脂血症、高胆固醇血症、脂质代谢异常和其他脂质紊乱，并延缓或降低与这些疾病相关的疾病和后遗症的发生风险，如动脉粥样硬化。
• [EN] COMPOUNDS FOR THE TREATMENT OF DYSLIPIDEMIA AND OTHER LIPID DISORDERS<br/>[FR] COMPOSES POUR TRAITEMENT DE LA DYSLIPIDEMIE ET AUTRES TROUBLES LIPIDIQUES
  申请人：MERCK & CO INC

  公开号：WO2006033891A3

  公开（公告）日：2007-02-01
• COMPOUNDS FOR THE TREATMENT OF DYSLIPIDEMIA AND OTHER LIPID DISORDERS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1796665B1

  公开（公告）日：2010-11-17