4-bromo-1-(naphthalen-1-yl)butan-1-one | 128113-41-7

• 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-bromo-1-(naphthalen-1-yl)butan-1-one
• 英文别名: 4-bromo-1-naphthalen-1-ylbutan-1-one
• CAS: 128113-41-7
• 化学式: C₁₄H₁₃BrO
• 分子量: 277.161
• InChiKey: HUHHBTJDYLAPTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-1-(naphthalen-1-yl)butan-1-one 、 2-巯基-5-(三氟甲基)吡啶 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 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：

  4-hydroxy-1-(naphthalen-1-yl)butan-1-one 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 18.67h， 生成 4-bromo-1-(naphthalen-1-yl)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

文献信息

• Transition‐Metal‐Free Ring‐Opening Reaction of 2‐Halocyclobutanols through Ring Contraction
  作者：Petr Oeser、Tereza Edlová、Marek Čubiňák、Tomáš Tobrman

  DOI：10.1002/ejoc.202100837

  日期：2021.9.21

  conditions for the thermal isomerization of cyclobutanols depend on the relative configuration of halohydrins. Based on the experiments performed, we assume that the halocyclobutanols undergo ring contraction to form cyclopropyl ketones, which are isomerized by means of hydrogen halide.

  我们开发了一种通过卤代环丁醇热开裂制备芳基烷基酮和α,β-不饱和酮的新方法。环丁醇热异构化的反应条件取决于卤代醇的相对构型。基于所进行的实验，我们假设卤代环丁醇发生缩环形成环丙基酮，后者通过卤化氢异构化。
• Visible-Light-Enhanced Ring Opening of Cycloalkanols Enabled by Brønsted Base-Tethered Acyloxy Radical Induced Hydrogen Atom Transfer-Electron Transfer
  作者：Rong Zhao、Yuan Yao、Dan Zhu、Denghu Chang、Yang Liu、Lei Shi

  DOI：10.1021/acs.orglett.8b00161

  日期：2018.2.16

  A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, is presented. This method produces diverse γ, δ, and even more remotely halogenated ketones in moderate to excellent yields under mild conditions. Interestingly, experimental and computational studies demonstrate the novel ring size-dependent concerted/stepwise (four-/five-

  提出了结合了PPO / TBAX氧化剂系统和蓝色LED辐射的无金属环烷醇开环/卤化反应。该方法在温和条件下以中等至极佳的收率生产出多种γ，δ甚至更遥远的卤代酮。有趣的是，实验和计算研究表明，布朗斯台德碱式束缚的酰氧基基团诱导了新颖的环尺寸依赖性的一致/逐步（四元/五元至五元至八元环）氢原子转移-电子转移，这表明氢氧自由基带来了明显的优势。二酰基过氧化物的环状结构。
• Photolyses of (3-naphthoxypropyl)-, (4-naphthylbutyl)-, and (4-naphthyl-4-oxobutyl)cobaloxime
  作者：Masaru Tada、Mitsunori Hiratsuka、Hiroyuki Goto

  DOI：10.1021/jo00301a030

  日期：1990.7
• TADA, MASARU;HIRATSUKA, MITSUNORI;GOTO, HIROYUKI, J. ORG. CHEM., 55,(1990) N4, C. 4363-4370
  作者：TADA, MASARU、HIRATSUKA, MITSUNORI、GOTO, HIROYUKI

  DOI：——

  日期：——