4-hydroxy-1-(naphthalen-1-yl)butan-1-one | 1272319-98-8

• 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: 4-hydroxy-1-(naphthalen-1-yl)butan-1-one
• 英文别名: 4-Hydroxy-1-naphthalen-1-ylbutan-1-one；4-hydroxy-1-naphthalen-1-ylbutan-1-one
• CAS: 1272319-98-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: NUIGEMFSFOFRSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  4-hydroxy-1-(naphthalen-1-yl)butan-1-one 在 三溴化磷 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.67h， 生成 1-(naphthalen-1-yl)-4-((5-(trifluoromethyl)pyridin-2-yl)thio)butan-1-one
  参考文献：
  名称：

  Synthesis of 5-trifluoromethyl-2-sulfonylpyridine PPARβ/δ antagonists: Effects on the affinity and selectivity towards PPARβ/δ

  摘要：

  The covalent modification of peroxisome-proliferator activated receptor beta/delta (PPAR beta/delta) is part of the mode of action of 5-trifluoromethyl-2-sulfonylpyridine PPAR beta/delta antagonists such as GSK3787 and CC618. Herein, the synthesis and in vitro biological evaluation of a range of structural analogues of the two antagonists are reported. The new ligands demonstrate that an improvement in the selectivity of 5-trifluoromethyl-2-sulfonylpyridine antagonists towards PPAR beta/delta is achievable at the expense of their immediate affinity for PPAR beta/delta. However, their putatively covalent and irreversible mode of action may ensure their efficacy over time, as observed in time-resolved fluorescence resonance energy transfer (TR-FRET)-based ligand displacement assays. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.012
• 作为产物：
  描述：

  1-(1-萘基)环丁醇 在 碘苯二乙酸 、 水 作用下， 以 六氟异丙醇 为溶剂， 反应 0.25h， 以57%的产率得到4-hydroxy-1-(naphthalen-1-yl)butan-1-one
  参考文献：
  名称：

  Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones

  摘要：

  Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of gamma-hydroxy ketones, is described. When using 2-substituted cyclobutanols, gamma-substituted gamma-hydroxy ketones are obtained through regioselective C-C bond cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.032

文献信息

• Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: evaluation of antibacterial and antifungal activities along with docking studies
  作者：Nisar A. Mir、Panduga Ramaraju、Satheeshvarma Vanaparthi、Sachin Choudhary、Rajnish P. Singh、Preetika Sharma、Rajni Kant、Rajpal Singh、Murugesan Sankaranarayanan、Indresh Kumar

  DOI：10.1039/d0nj03575k

  日期：——

  A sequential multicomponent method is developed to access highly substituted N-arylpyrrole-3-carbaldehydes and tested for antibacterial and antifungal activities against bacterial strains.

  开发了一种顺序多组分方法，用于合成高度取代的N-芳基吡咯-3-甲醛，并针对细菌菌株进行抗菌和抗真菌活性测试。
• Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(<scp>ii</scp>) glycine complex under microwave irradiation
  作者：Juan C. Jiménez-Cruz、Ramón Guzmán-Mejía、Eusebio Juaristi、Omar Sánchez-Antonio、Marco A. García-Revilla、J. Betzabe González-Campos、Judit Aviña-Verduzco

  DOI：10.1039/d0nj02630a

  日期：——

  A series of aromatic γ-hydroxyketones were prepared by means of Heck coupling reaction of aryl halides and 2,3-dihydrofuran, catalyzed by PdCl2·Gly2 and under microwave irradiation. This synthetic transformation involves the formation of an aryl-dihydrofuranoic intermediate, followed by an unusual opening of the heterocycle promoted by a water molecule and the formation of the ketone carbonyl function

  在PdCl 2 ·Gly 2催化和微波辐射下，通过芳基卤化物与2，3-二氢呋喃的Heck偶联反应，制备了一系列芳族γ-羟基酮。这种合成转化涉及形成芳基-二氢呋喃基中间体，然后由水分子促进杂环的异常打开，并通过酮-烯醇互变异构作用形成酮羰基官能团。
• Synthesis of 5-trifluoromethyl-2-sulfonylpyridine PPARβ/δ antagonists: Effects on the affinity and selectivity towards PPARβ/δ
  作者：Åsmund Kaupang、Eili Tranheim Kase、Cecilie Xuan Trang Vo、Marthe Amundsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.bmc.2015.12.012

  日期：2016.1

  The covalent modification of peroxisome-proliferator activated receptor beta/delta (PPAR beta/delta) is part of the mode of action of 5-trifluoromethyl-2-sulfonylpyridine PPAR beta/delta antagonists such as GSK3787 and CC618. Herein, the synthesis and in vitro biological evaluation of a range of structural analogues of the two antagonists are reported. The new ligands demonstrate that an improvement in the selectivity of 5-trifluoromethyl-2-sulfonylpyridine antagonists towards PPAR beta/delta is achievable at the expense of their immediate affinity for PPAR beta/delta. However, their putatively covalent and irreversible mode of action may ensure their efficacy over time, as observed in time-resolved fluorescence resonance energy transfer (TR-FRET)-based ligand displacement assays. (c) 2015 Elsevier Ltd. All rights reserved.
• Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones
  作者：Hiromichi Fujioka、Hideyuki Komatsu、Akihito Miyoshi、Kenichi Murai、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2010.12.032

  日期：2011.3

  Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of gamma-hydroxy ketones, is described. When using 2-substituted cyclobutanols, gamma-substituted gamma-hydroxy ketones are obtained through regioselective C-C bond cleavage. (C) 2010 Elsevier Ltd. All rights reserved.