3-allyl-2-(2,6-dichlorobenzyloxy)benzaldehyde | 263754-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-allyl-2-(2,6-dichlorobenzyloxy)benzaldehyde
• 英文别名: 2-[(2,6-Dichlorophenyl)methoxy]-3-prop-2-enylbenzaldehyde
• CAS: 263754-53-6
• 化学式: C₁₇H₁₄Cl₂O₂
• 分子量: 321.203
• InChiKey: WHRSNLPVCYNWKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  442.1±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allyl-2-(2,6-dichlorobenzyloxy)benzaldehyde 在 四丁基氯化铵 palladium diacetate 、 lithium acetate 、 二异丁基氢化铝 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 生成 (E)-3-(2-{(E)-3-[2-(2,6-Dichloro-benzyloxy)-3-hydroxymethyl-phenyl]-allyl}-phenyl)-acrylic acid
  参考文献：
  名称：

  Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists

  摘要：

  A series of novel ortho-substituted cinnamic acids have been synthesized, and their binding activity and selectivity on the four prostaglandin E, receptors evaluated. Many of them are very potent and selective EP3 antagonists (K-i 3-10 nM), while compound 9 is a very good and selective EP2 agonist (K-i 8 nM). The biological profile of the EP2 agonist 9 in vivo and the metabolic profile of selected EP3 antagonists are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.051
• 作为产物：
  描述：

  邻丙烯基氧基苯甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 16.0h， 生成 3-allyl-2-(2,6-dichlorobenzyloxy)benzaldehyde
  参考文献：
  名称：

  Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists

  摘要：

  A series of novel ortho-substituted cinnamic acids have been synthesized, and their binding activity and selectivity on the four prostaglandin E, receptors evaluated. Many of them are very potent and selective EP3 antagonists (K-i 3-10 nM), while compound 9 is a very good and selective EP2 agonist (K-i 8 nM). The biological profile of the EP2 agonist 9 in vivo and the metabolic profile of selected EP3 antagonists are also reported. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.051

文献信息

• Prostaglandin receptor ligands
  申请人：Merck Frosst Canada & Co.

  公开号：US20010031766A1

  公开（公告）日：2001-10-18

  Compounds and methods for treating prostaglandin mediated diseases, and certain pharmaceutical compositions thereof are disclosed. The compounds are represented by formula II: Ar 1 —W—Ar 2 —X—Q  II The compounds of the invention are structurally different from NSAIDs and opiates, and are antagonists of the pain and inflammatory effects of E-type prostaglandins.

  本发明揭示了用于治疗前列腺素介导的疾病的化合物和方法，以及某些制药组合物。该化合物由公式II表示：Ar1-W-Ar2-X-Q，本发明的化合物在结构上不同于NSAIDs和鸦片类药物，并且是E型前列腺素疼痛和炎症效应的拮抗剂。
• PROSTAGLANDIN RECEPTOR LIGANDS
  申请人：Merck Frosst Canada & Co.

  公开号：EP1119542A1

  公开（公告）日：2001-08-01
• US6211197B1
  申请人：——

  公开号：US6211197B1

  公开（公告）日：2001-04-03
• [EN] PROSTAGLANDIN RECEPTOR LIGANDS<br/>[FR] LIGANDS DES RECEPTEURS DES PROSTAGLANDINES
  申请人：MERCK FROSST CANADA INC

  公开号：WO2000020371A1

  公开（公告）日：2000-04-13

  Compounds and methods for treating prostaglandin mediated diseases, and certain pharmaceutical compositions thereof are disclosed. The compounds are represented by formula (II): Ar1-W-Ar2-X-Q. The compounds of the invention are structurally different from NSAIDs and opiates, and are antagonists of the pain and inflammatory effects of E-type prostaglandins.
• Structure–activity relationship studies on ortho-substituted cinnamic acids, a new class of selective EP3 antagonists
  作者：Michel Belley、Michel Gallant、Bruno Roy、Karine Houde、Nicolas Lachance、Marc Labelle、Laird A. Trimble、Nathalie Chauret、Chun Li、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Gillian M. Greig、Deborah Slipetz、Kathleen M. Metters、Robert Gordon、Chi Chung Chan、Robert J. Zamboni

  DOI：10.1016/j.bmcl.2004.11.051

  日期：2005.2

  A series of novel ortho-substituted cinnamic acids have been synthesized, and their binding activity and selectivity on the four prostaglandin E, receptors evaluated. Many of them are very potent and selective EP3 antagonists (K-i 3-10 nM), while compound 9 is a very good and selective EP2 agonist (K-i 8 nM). The biological profile of the EP2 agonist 9 in vivo and the metabolic profile of selected EP3 antagonists are also reported. (C) 2004 Elsevier Ltd. All rights reserved.