(E)-3-(2-((naphthalen-3-yl)methyl)phenyl)acrylic acid | 244103-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2-((naphthalen-3-yl)methyl)phenyl)acrylic acid
• 英文别名: (E)-3-[2-(2-naphthylmethyl)phenyl]-2-propenoic acid；3-(2-(Naphthalen-2-ylmethyl)phenyl)acrylic acid；(E)-3-[2-(naphthalen-2-ylmethyl)phenyl]prop-2-enoic acid
• CAS: 244103-25-1
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: MOLQZQYMXCCLHS-VAWYXSNFSA-N

物化性质

• 熔点：
  160-161 °C(Solv: hexane (110-54-3))
• 沸点：
  490.8±14.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲氧基苯磺酰胺 、 (E)-3-(2-((naphthalen-3-yl)methyl)phenyl)acrylic acid 在 4-二甲氨基吡啶 、 N,N'-1,2-ethylenediylbis-(L-cysteine) diethyl ester dihydrochloride 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 以73%的产率得到L-798106
  参考文献：
  名称：

  Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor

  摘要：

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00110-9
• 作为产物：
  描述：

  methyl (E)-3-(2’-(bromomethyl)phenyl)acrylate 在 sodium hydroxide 、 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 14.0h， 生成 (E)-3-(2-((naphthalen-3-yl)methyl)phenyl)acrylic acid
  参考文献：
  名称：

  Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor

  摘要：

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00110-9

文献信息

• Three-Component Coupling of Benzyne:  Domino Intermolecular Carbopalladation
  作者：Jaclyn L. Henderson、Andrew S. Edwards、Michael F. Greaney

  DOI：10.1021/ja0615526

  日期：2006.6.1

  A new three-component coupling reaction of benzyne is described that uses two intermolecular carbopalladation reactions to produce 1,2-functionalized benzene derivatives.

  介绍了一种新的三组分苯偶合反应，该反应使用两个分子间碳钯化反应来生产 1,2-官能化苯衍生物。
• Structure–activity relationship on the human EP3 prostanoid receptor by use of solid-support chemistry
  作者：Hélène Juteau、Yves Gareau、Marc Labelle、Sonia Lamontagne、Nathalie Tremblay、Marie-Claude Carrière、Nicole Sawyer、Danielle Denis、Kathleen M. Metters

  DOI：10.1016/s0960-894x(01)00056-7

  日期：2001.3

  Potent and selective EP3 receptor ligands were found by making a library using solid-support chemistry. These compounds can be obtained by a Suzuki coupling reaction of a solid-supported benzyl bromide using various boronic acids. The yields obtained for this reaction were in the range of 24-95% of arylmethyl cinnamic acid 1 after cleavage from the Wang resin. (C) 2001 Published by Elsevier Science Ltd.
• US6242493B1
  申请人：——

  公开号：US6242493B1

  公开（公告）日：2001-06-05
• Structure–activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor
  作者：Hélène Juteau、Yves Gareau、Marc Labelle、Claudio F Sturino、Nicole Sawyer、Nathalie Tremblay、Sonia Lamontagne、Marie-Claude Carrière、Danielle Denis、Kathleen M Metters

  DOI：10.1016/s0968-0896(01)00110-9

  日期：2001.8

  Potent and selective antagonists of the human EP3 receptor have been identified. The structure-activity relationship of the chemical series was conducted and we found several analogues displaying sub-nanomolar K-i values at the EP3 receptor and micromolar activities at the EP1, EP2 and EP4 receptors. The effect of added human serum albumin (HSA) on the binding affinity at the EP3 receptor was also investigated. (C) 2001 Elsevier Science Ltd. All rights reserved.