2-(4-nitrophenoxy)biphenyl | 130955-65-6

• 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: 2-(4-nitrophenoxy)biphenyl
• 英文别名: biphenyl-2-yl-(4-nitro-phenyl)-ether；Biphenyl-2-yl-(4-nitro-phenyl)-aether；4-Nitro-1-(biphenylyl-(2)-oxy)-benzol；2-(4-Nitro-phenoxy)-biphenyl；1-(4-Nitrophenoxy)-2-phenylbenzene
• CAS: 130955-65-6
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: IEUOLWSEWQNOFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenoxy)biphenyl 在 碳酸氢钠 、 sodium hydroxide 、 锌 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 2.33h， 生成 (S)-2-(1-(4-(biphenyl-2-yloxy)phenyl)pyrrolidin-2-yl)acetic acid hydrochloride
  参考文献：
  名称：

  Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

  摘要：

  A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding K-i and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both G(q)-coupled intracellular Ca2+ flux and G(s)-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

  DOI：

  10.1021/acs.jmedchem.6b01559
• 作为产物：
  描述：

  对硝基氯苯 以76%的产率得到
  参考文献：
  名称：

  Shao Yuchang, Yang Jinzong, Huaxue shiji (Chem. Reagents), 16 (1994) N 5, S 305-306

  摘要：

  DOI：

文献信息

• Metal- and ligand-free Ullmann-type C–O and C–N coupling reactions promoted by potassium tert-butoxide
  作者：Shuliang Yang、Cunqi Wu、Mingbo Ruan、Yanqin Yang、Yongxia Zhao、Jiajia Niu、Wei Yang、Jingwei Xu

  DOI：10.1016/j.tetlet.2012.05.131

  日期：2012.8

  A simple, metal- and ligand-free procedure for the Ullmann-type C–O coupling reactions has been achieved by allowing aryl bromides to react with a variety of phenols in the presence of t-BuOK. Moderate to excellent yields of O-arylation products are obtained under mild conditions in a short time. In addition, two examples of C–N coupling reactions are also reported. A benzyne mechanism is proposed

  通过使芳基溴化物在t- BuOK存在下与多种酚反应，已实现了用于Ullmann型C-O偶联反应的简单，无金属和配体的方法。在温和的条件下，在短时间内即可获得中等至极好的O-芳基化产物收率。此外，还报道了两个C–N偶联反应的例子。根据实验数据提出了苯并yne机理。
• US2095619
  申请人：——

  公开号：——

  公开（公告）日：——
• Luettringhaus; v. Saeaef, Justus Liebigs Annalen der Chemie, 1939, vol. 542, p. 241,257
  作者：Luettringhaus、v. Saeaef

  DOI：——

  日期：——
• NOVEL PROSTAGLANDIN SYNTHASE INHIBITORS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0783486A1

  公开（公告）日：1997-07-16
• US5593994A
  申请人：——

  公开号：US5593994A

  公开（公告）日：1997-01-14