4-[3-(3-羟丙基)苯氧基]丁酸乙酯 | 1034020-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-[3-(3-羟丙基)苯氧基]丁酸乙酯
• 英文名称: ethyl 4-[3-(3-hydroxypropyl)phenoxy]butanoate
• CAS: 1034020-28-4
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: VJWRKGCVDNXCED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  4-[3-(3-羟丙基)苯氧基]丁酸乙酯 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 40.0h， 生成 ethyl 4-{3-[3-(3-benzhydryl-6-oxo-1,6-dihydropyridazin-1-yl)propyl]phenoxy}butanoate
  参考文献：
  名称：

  Development of a Practical and Scalable Synthesis of a Potent CRTH2 Antagonist

  摘要：

  This contribution describes the process research and development of a practical and scalable synthetic method towards compound 1, which has a potent CRTH2 antagonistic activity. The medicinal chemistry synthetic route and second generation synthetic route had several issues in scale-up synthesis. In contrast, the synthetic method described here does not require purification by column chromatography for all steps, and the formation of impurities is suppressed well. This highly efficient and scalable process was successfully demonstrated in the large-scale synthesis of 1.

  DOI：

  10.1021/op3001492
• 作为产物：
  描述：

  3-(3-羟基苯基)丙酸 在 potassium carbonate 、 红铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 4-[3-(3-羟丙基)苯氧基]丁酸乙酯
  参考文献：
  名称：

  Development of a Practical and Scalable Synthesis of a Potent CRTH2 Antagonist

  摘要：

  This contribution describes the process research and development of a practical and scalable synthetic method towards compound 1, which has a potent CRTH2 antagonistic activity. The medicinal chemistry synthetic route and second generation synthetic route had several issues in scale-up synthesis. In contrast, the synthetic method described here does not require purification by column chromatography for all steps, and the formation of impurities is suppressed well. This highly efficient and scalable process was successfully demonstrated in the large-scale synthesis of 1.

  DOI：

  10.1021/op3001492

文献信息

• POLYCYCLIC ACID COMPOUNDS USEFUL AS CRTH2 ANTAGONISTS AND ANTIALLERGIC AGENTS
  申请人：Terasaka Tadashi

  公开号：US20100009991A1

  公开（公告）日：2010-01-14

  The present invention relates to a novel compound or a salt thereof, which is useful as a CRTH2 antagonist, especially as a medicament for disorder that participates eosinophil, for example, allergic disorder such as asthma, allergic rhinitis, allergic dermatitis, conjunctival inflammation, hives, eosinophilic bronchitis, food allergy, inflammation of the nasal sinuses, multiple sclerosis, angiitis, or chronic obstructive pulmonary disease (COPD) and the like.

  本发明涉及一种新型化合物或其盐，该化合物可作为CRTH2拮抗剂使用，特别是作为治疗参与嗜酸性粒细胞的疾病的药物，例如哮喘、过敏性鼻炎、过敏性皮炎、结膜炎、荨麻疹、嗜酸性支气管炎、食物过敏、鼻窦炎炎症、多发性硬化症、血管炎或慢性阻塞性肺疾病（COPD）等疾病。
• US8273745B2
  申请人：——

  公开号：US8273745B2

  公开（公告）日：2012-09-25
• [EN] POLYCYCLIC ACID COMPOUNDS USEFUL AS CRTH2 ANTAGONISTS AND ANTIALLERGIC AGENTS<br/>[FR] NOUVEAU COMPOSÉ D' OXYCARBONYLE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2008072784A1

  公开（公告）日：2008-06-19

  [EN] The present invention relates to a novel compound or a salt thereof, which is useful as a CRTH2 antagonist, especially as a medicament for disorder that participates eosinophil, for example, allergic disorder such as asthma, allergic rhinitis, allergic dermatitis, conjunctival inflammation, hives, eosinophilic bronchitis, food allergy, inflammation of the nasal sinuses, multiple sclerosis, angiitis, or chronic obstructive pulmonary disease (COPD) and the like.
  [FR] La présente invention concerne un nouveau composé ou un de ses sels, qui est utile comme antagoniste du CRTH2, en particulier comme médicament destiné au traitement d'un trouble lié aux éosinophiles, tel qu'un trouble allergique comme l'asthme, la rhinite allergique, la dermatite allergique, la conjonctivite, l'urticaire, la bronchite à éosinophiles, l'allergie alimentaire, l'inflammation des sinus paranasaux, la sclérose en plaques, l'angéite ou la maladie pulmonaire obstructive chronique (MPOC) et analogue, par exemple.
• Development of a Practical and Scalable Synthesis of a Potent CRTH2 Antagonist
  作者：Shinya Yoshida、Toshitaka Yoshino、Akio Miyafuji、Hironobu Yasuda、Takenori Kimura、Takumi Takahashi、Takashi Mukuta

  DOI：10.1021/op3001492

  日期：2012.9.21

  This contribution describes the process research and development of a practical and scalable synthetic method towards compound 1, which has a potent CRTH2 antagonistic activity. The medicinal chemistry synthetic route and second generation synthetic route had several issues in scale-up synthesis. In contrast, the synthetic method described here does not require purification by column chromatography for all steps, and the formation of impurities is suppressed well. This highly efficient and scalable process was successfully demonstrated in the large-scale synthesis of 1.