6-phenyl-2-naphthoic acid | 855207-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-phenyl-2-naphthoic acid
• 英文别名: 6-Phenylnaphthalene-2-carboxylic acid
• CAS: 855207-53-3
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: BNMIGHLFXDYZGD-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  439.2±14.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6-phenyl-2-naphthoic acid 在 氯化亚砜 、 sodium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 18.0h， 生成 (2RS,3SR)-1-(6-phenylnaphthalene-2-carbonyl)piperazine-2,3-dicarboxylic acid
  参考文献：
  名称：

  Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors

  摘要：

  Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.

  DOI：

  10.1021/jm201230z
• 作为产物：
  描述：

  6-bromonaphthalen-2-yl pivalate 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1'-双(二苯基膦)二茂铁 、 锰 、 potassium phosphate 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 作用下， 以 N,N-二甲基乙酰胺 、 水 、 甲苯 为溶剂， 80.0~90.0 ℃ 、101.33 kPa 条件下， 反应 60.0h， 生成 6-phenyl-2-naphthoic acid
  参考文献：
  名称：

  镍催化 C(sp2)– 和 C(sp3)–O 键与 CO2 的羧化

  摘要：

  近年来，芳基卤化物和苄基卤化物与 CO2 的羧化取得了重大进展，成为使用化学计量量明确的金属物质的方便替代品。然而，这些过程中的大多数都需要使用自燃和空气敏感试剂，目前的方法主要限于有机卤化物。因此，非常希望发现一种温和的、操作简单的替代羧化反应，该羧化反应在广泛的底物范围内使用容易获得的偶联伙伴发生。在此，我们报告了一种新的协议，该协议涉及 CO2 协同活化的开发和惰性 C(sp(2))-O 和 C(sp(3))-O 键的相当具有挑战性的活化，这些键源自简单且廉价的酒精，这是该领域以前未被认识到的机会。这种前所未有的羧化事件的特点是其简单、温和的反应条件、显着的选择性模式以及使用对空气、水分不敏感且易于处理的镍预催化剂的优异化学选择性曲线。我们的结果使我们的方法成为一种强大的替代方案，实用性和新颖性，可以替代常用的有机卤化物作为羧化方案中的对应物。此外，这项研究首次表明，无痕导向基团允许在没有扩展

  DOI：

  10.1021/ja410883p

文献信息

• Impact of Solvent and Their Contaminants on Pd/C Catalyzed <i>Suzuki‐Miyaura</i> Cross‐Coupling Reactions
  作者：Alexandre Lambert de Boisjan、Christophe Allemann、Luca Fadini

  DOI：10.1002/hlca.202100035

  日期：2021.6

  work was to understand if solvent contaminants can interfere in Suzuki’s cross-coupling reactions and if it can explain the lack of robustness in industrial processes. For this purpose, several parameters were tested on the industrial model reaction between 2-bromonaphthalene and phenylboronic acid catalyzed by Pd/C. Best results were obtained using THF as solvent. Traces of the precursors of the used

  这项工作的目的是了解溶剂污染物是否会干扰Suzuki的交叉偶联反应，以及它是否可以解释工业过程缺乏稳健性。为此，在 Pd/C 催化的 2-溴萘和苯基硼酸之间的工业模型反应中测试了几个参数。使用 THF 作为溶剂获得了最佳结果。所用溶剂的痕量前体，如 2,3-二氢呋喃或马来酸酐（与溶剂相关的 100-300 ppm）强烈毒害反应，显着降低转化率。这意味着要确保稳定的生产，必须在 ppm 级分析溶剂质量。幸运的是，添加三苯基膦可以避免催化剂中毒。
• Norvaline Derivative and Method for Preparation Thereof
  申请人：Harada Naoyuki

  公开号：US20080076769A1

  公开（公告）日：2008-03-27

  Norvaline derivative of the formula [I] or pharmaceutically acceptable salt thereof, method for preparing the same, pharmaceutical composition containing the same, and use of said compound for inhibiting transporting activity of glycine transporter type 2 (GlyT2). [wherein X is —CH 2 —, —O—, —S— or single bond; Ar is optionally substituted aryl or lower cycloalkyl; n is 0 to 2; R 1 and R 2 are (i) each is hydrogen or lower alkyl; (ii) R 1 and R 2 are combined to form lower alkylene; or (iii) R 1 is hydrogen or lower alkyl and R 2 is combined with R 4 or R 6 to form lower alkylene; R 3 and R 4 are (i) each is hydrogen or lower alkyl; (ii) R 3 and R 4 are combined to form lower alkylene; or (iii) R 3 is hydrogen or lower alkyl and R 4 is combined with R 2 or R 6 to form lower alkylene; R is or —OR 7 ; R 5 and R 6 are (i) each is optionally substituted lower alkyl, or hydrogen; (ii) R 5 and R 6 are combined to form aliphatic 5- to 6-membered heterocyclic group; or (iii) R 5 is optionally substituted lower alkyl or hydrogen and R 6 is combined with R 2 or R 4 to form lower alkylene; R 7 is lower alkyl.

  Norvaline衍生物的化学式[I]或其药学上可接受的盐，制备方法，含有该化合物的药物组合物，以及用于抑制甘氨酸转运体2型（GlyT2）的转运活性的用途。[其中X为-CH2-，-O-，-S-或单键；Ar为可选取代芳基或较低的环烷基；n为0至2；R1和R2为（i）氢或较低的烷基；（ii）R1和R2结合形成较低的烷基；或（iii）R1为氢或较低的烷基，R2与R4或R6结合形成较低的烷基；R3和R4为（i）氢或较低的烷基；（ii）R3和R4结合形成较低的烷基；或（iii）R3为氢或较低的烷基，R4与R2或R6结合形成较低的烷基；R为-OH或-OR7；R5和R6为（i）可选取代的较低烷基或氢；（ii）R5和R6结合形成脂肪族5-至6-成员杂环基；或（iii）R5为可选取代的较低烷基或氢，R6与R2或R4结合形成较低的烷基；R7为较低烷基。
• Octahydro-cyclobuta[1,2-c;3,4-c′]dipyrrol-2-yl
  申请人：Hoffmann-La Roche Inc.

  公开号：US10849881B2

  公开（公告）日：2020-12-01

  The invention provides novel compounds having the general formula (I) wherein R1, Y and R2 are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供了具有通式 (I) 的新型化合物 其中 R1、Y 和 R2 如本文所述，提供了包括这些化合物的组合物和使用这些化合物的方法。
• Palladium charcoal-catalyzed, ligandless Suzuki reaction by using tetraarylborates in water
  作者：Gang Lu、Robert Franzén、Qian Zhang、Youjun Xu

  DOI：10.1016/j.tetlet.2005.04.022

  日期：2005.6

  In water and without using any ligand, palladium charcoal-catalyzed Suzuki coupling reaction of tetraarylborates with aryl bromides could be achieved in excellent yield. A concise mechanism consisting of four catalytic cycles is depicted in this paper. (c) 2005 Elsevier Ltd. All rights reserved.
• WO2006/80477
  申请人：——

  公开号：——

  公开（公告）日：——