4-bromo-1-(naphthalen-2-yl)butan-1-one | 128113-42-8

• 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-bromo-1-(naphthalen-2-yl)butan-1-one
• 英文别名: 4-bromo-1-naphthalen-2-ylbutan-1-one
• CAS: 128113-42-8
• 化学式: C₁₄H₁₃BrO
• 分子量: 277.161
• InChiKey: RCIHLTISTLDDHD-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-2-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-2-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：

  2-溴萘 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 21.09h， 生成 4-bromo-1-(naphthalen-2-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

• Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
  作者：Yiqiong Wang、Fei Huang、Songlin Zhang

  DOI：10.1002/ejoc.202000678

  日期：2020.8.31

  A general, efficient, and experimentally simple one‐pot new method for the synthesis of cyclic imines through intramolecular cyclization of brominated oxime ether promoted by ytterbium(0) was reported for the first time. In this new strategy for the construction of cyclic imines, the N–O bond is used as a receptor of ytterbium reagent rather than as a source of N‐centred radical.

  首次报道了通过，（0）促进的溴化肟醚分子内环化合成环亚胺的通用，高效且实验简单的新方法。在这种构建环状亚胺的新策略中，N-O键用作as试剂的受体，而不是N-中心自由基的来源。
• Iminyl Radicals by Reductive Cleavage of N–O Bond in Oxime Ether Promoted by SmI₂: A Straightforward Synthesis of Five-Membered Cyclic Imines
  作者：Fei Huang、Songlin Zhang

  DOI：10.1021/acs.orglett.9b02740

  日期：2019.9.20

  A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient

  首次报道了由SmI2促进的肟醚中NO键的还原性裂解形成的一种以N为中心的自由基的新方法。原位生成的N中心自由基经过分子内环化以两种方式提供五元环亚胺：N中心自由基加成和N中心阴离子亲核取代。从合成的观点出发，开发了一种有效的五元环亚胺的合成方法。提出了一种转化机制。
• 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：——