1-(4-(3-methoxyphenoxy)phenyl)ethan-1-one | 93899-01-5

• 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: 1-(4-(3-methoxyphenoxy)phenyl)ethan-1-one
• 英文别名: 4'-(3-Methoxyphenoxy)acetophenone；1-[4-(3-methoxyphenoxy)phenyl]ethanone
• CAS: 93899-01-5
• 化学式: C₁₅H₁₄O₃
• mdl: MFCD01627703
• 分子量: 242.274
• InChiKey: MCUKBEHWHRIHMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(3-methoxyphenoxy)phenyl)ethan-1-one 在 吡啶 、 氢氧化钾 、 ammonium hydroxide 、 sulfur 作用下， 生成 [4-(3-methoxy-phenoxy)-phenyl]-acetic acid
  参考文献：
  名称：

  Tomita; Watanabe, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 52

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基苯酚 、 4-溴苯乙酮 在 copper(l) iodide 硅酸四乙酯 、 caesium carbonate 作用下， 以88%的产率得到1-(4-(3-methoxyphenoxy)phenyl)ethan-1-one
  参考文献：
  名称：

  原硅酸四乙酯中的Ullmann反应：三芳基胺和二芳基醚的新型合成。

  摘要：

  报道了一种新颖的三芳基胺和二芳基醚的合成方法。该方法的一个特点是在原硅酸四乙酯中无配体的铜催化的CN和CO键的形成。

  DOI：

  10.1039/b706449g

文献信息

• Diaryl Ether Formation Merging Photoredox and Nickel Catalysis
  作者：Le Liu、Cristina Nevado

  DOI：10.1021/acs.organomet.1c00018

  日期：2021.7.26

  Photoredox and Ni catalysis are combined to produce diaryl ethers under mild conditions. A broad range of aryl halides and phenol derivatives are cross-coupled in the presence of a readily available organic photocatalyst and NiBr2(dtbpy). Symmetrical diaryl ethers have also been directly obtained from aryl bromides in the presence of water. Mechanistic investigations support the involvement of Ni(0)

  Photoredox 和 Ni 催化在温和条件下结合产生二芳基醚。在容易获得的有机光催化剂和 NiBr 2 (dtbpy)存在下，广泛的芳基卤化物和苯酚衍生物交叉偶联。对称二芳基醚也已在水存在下由芳基溴化物直接获得。机理研究支持在反应开始时 Ni(0) 物质的参与以及在生产性 C(sp 2 )-OAr 还原消除之前的 Ni(II)/Ni(III) 光催化单电子转移过程。
• Structure–Reactivity Relationships on Substrates and Inhibitors of the Lysine Deacylase Sirtuin 2 from <i>Schistosoma mansoni</i> (<i>Sm</i>Sirt2)
  作者：Daria Monaldi、Dante Rotili、Julien Lancelot、Martin Marek、Nathalie Wössner、Alessia Lucidi、Daniela Tomaselli、Elizabeth Ramos-Morales、Christophe Romier、Raymond J. Pierce、Antonello Mai、Manfred Jung

  DOI：10.1021/acs.jmedchem.9b00638

  日期：2019.10.10

  vitro screening of the GSK Kinetobox library and structure–activity relationships of identified hits led to the first SmSirt2 inhibitors with activity in the low micromolar range. Several SmSirt2 inhibitors showed potency against both larval schistosomes (viability) and adult worms (pairing, egg laying) in culture without general toxicity to human cancer cells.

  目前可用于治疗被忽视的血吸虫病的唯一药物是吡喹酮，耐药性的出现使得对新型治疗剂的研究变得必要和紧迫。为此，靶向曼氏血吸虫表观遗传酶（其调节寄生虫的生命周期）作为一种有前途的方法应运而生。由于人类sirtuin抑制剂对寄生虫存活和繁殖的强烈影响，血吸虫sirtuins被认为是潜在的治疗靶标。曼氏沙门氏菌sirtuin 2（Sm Sirt2）的合成底物的体外测试和肉豆蔻酰化肽的动力学实验证明赖氨酸长链脱酰作用是固有的SmSirt2活性除其首次已知的脱乙酰基酶活性外。对GSK Kinetobox文库进行集中的体外筛选以及已确定的基因敲击物的构效关系，导致了首批具有低微摩尔范围活性的Sm Sirt2抑制剂。几种Sm Sirt2抑制剂在培养中显示出对幼虫血吸虫（存活力）和成虫（配对，产卵）的效力，而对人癌细胞没有一般毒性。
• Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer
  作者：Da-Liang Zhu、Shan Jiang、Qi Wu、Hao Wang、Hai-Yan Li、Hong-Xi Li

  DOI：10.1021/acs.orglett.1c03066

  日期：2021.11.5

  arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one

  尽管在链烷醇和芳基卤化物的镍催化醚化方面取得了一些进展，但由于苯酚盐的还原电位低得多，从而抑制了镍 (II) 中间体氧化成必需的化合物，因此这种使用苯酚的镍催化转化为二芳基醚的能力并不成功Ni(III) 物种。我们在此报告了在可见光下使用t- BuNH( i- Pr) 作为碱和thioxanthen -9-one 作为光敏剂的可见光引发的镍催化苯酚与芳基卤化物的O-芳基化。这种光电耦合表现出广泛的基板范围。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
• Ullmann reaction in tetraethyl orthosilicate: a novel synthesis of triarylamines and diaryl ethers
  作者：Yuanhong Zhao、Yunsong Wang、Hongwei Sun、Liang Li、Hongbin Zhang

  DOI：10.1039/b706449g

  日期：——

  A novel synthesis of triarylamines and diaryl ethers is reported; a feature of this process is the ligand-free copper-catalysed C-N and C-O bond formation in tetraethyl orthosilicate.

  报道了一种新颖的三芳基胺和二芳基醚的合成方法。该方法的一个特点是在原硅酸四乙酯中无配体的铜催化的CN和CO键的形成。