3-allyl-2-(benzyloxy)toluene | 122030-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-allyl-2-(benzyloxy)toluene
• 英文别名: 2-(Benzyloxy)-1-methyl-3-(prop-2-en-1-yl)benzene；1-methyl-2-phenylmethoxy-3-prop-2-enylbenzene
• CAS: 122030-12-0
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: SUJMRCJGCXDRSA-UHFFFAOYSA-N

物化性质

• 沸点：
  340.3±11.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-allyl-2-(benzyloxy)toluene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.0h， 生成 (E)-3-{2-[3-(2-Benzyloxy-3-methyl-phenyl)-propyl]-phenyl}-acrylic acid methyl ester
  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：

  2-烯丙基-6-甲基苯酚 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-allyl-2-(benzyloxy)toluene
  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：US06211197B1

  公开（公告）日：2001-04-03

  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  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疾病的化合物和方法，以及某些制药组合物。这些化合物由式II表示：Ar1—W—Ar2—X—Q。该发明的化合物在结构上与非甾体类抗炎药和阿片类药物不同，是E型前列腺素的疼痛和炎症作用的拮抗剂。
• 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.