1-(4-(naphthalen-2-yloxy)phenyl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(naphthalen-2-yloxy)phenyl)ethan-1-one
• 英文别名: 1-(4-(naphthalen-2-yloxy)phenyl)ethanone；1-[4-(naphthalen-2-yloxy)phenyl]ethanone；1-(4-naphthalen-2-yloxyphenyl)ethanone
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: QJOJRJHBZDXZNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 1-(4-(naphthalen-2-yloxy)phenyl)ethan-1-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  6-(4′-Aryloxy-phenyl)vinyl-1,2,4-trioxanes: A new series of orally active peroxides effective against multidrug-resistant Plasmodium yoelii in Swiss mice

  摘要：

  A new series of 6-(4'-aryloxy-phenyl)vinyl-1,2,4-trioxanes 10a-d, 11a-d, and 12a-d have been synthesized and evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Trioxanes 10b and 10c, the two most active compounds of the series, provided 100% protection to the infected mice at 48 mg/kg x 4 days. Clinically useful drug beta-arteether provided 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively, in this model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.045
• 作为产物：
  描述：

  1-(4-fluorophenyl)-2-(naphthalen-2-yloxy)ethan-1-ol 在 RuH₂(CO)(PPh₃)₃ 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以86%的产率得到1-(4-(naphthalen-2-yloxy)phenyl)ethan-1-one
  参考文献：
  名称：

  探索串联钌催化的氢转移和S N Ar化学

  摘要：

  报道了一种通过电子芳烃活化对苯甲醇进行催化官能化的氢转移策略，该方法以优异的分离产率获得了各种定制的二芳基醚和芳基胺（38例，平均产率为70％）。利用氢转移方法，可以通过明智地选择简单和廉价的添加剂来选择功能化产物的氧化水平。

  DOI：

  10.1021/acs.orglett.7b03441

文献信息

• <i>N</i>,<i>N</i>-Dimethyl Glycine-Promoted Ullmann Coupling Reaction of Phenols and Aryl Halides
  作者：Dawei Ma、Qian Cai

  DOI：10.1021/ol0350947

  日期：2003.10.1

  [reaction: see text] Ullmann-type diaryl ether synthesis can be performed at 90 degrees C using either aryl iodides or aryl bromides as the substrates under the assistance of N,N-dimethylglycine.

  [反应：见正文] Ullmann型二芳基醚的合成可以在N，N-二甲基甘氨酸的帮助下，使用芳基碘化物或芳基溴化物作为底物，在90摄氏度下进行。
• Tris-(2-aminoethyl) amine as a novel and efficient tripod ligand for a copper(I)-catalyzed C–O coupling reaction
  作者：Nivrutti R. Jogdand、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2009.03.028

  日期：2009.7

  We have introduced a novel, efficient, commercially available and economically attractive N-donor tripod ligand, tris-(2-aminoethyl)amine for copper-catalyzed Ullmann diaryl ether synthesis. This catalyst system is highly active for both aryl iodides and aryl bromides. Variously substituted diaryl ethers have been synthesized in good to excellent yields.

  我们已经介绍了一种新颖，有效，可商购且在经济上有吸引力的N供体三脚架配体tris-（2-氨基乙基）胺，用于铜催化的Ullmann二芳基醚合成。该催化剂体系对芳基碘化物和芳基溴化物都具有高活性。已经以良好至优异的产率合成了各种取代的二芳基醚。
• 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides
  作者：Yatao Qiu、Weijun Jia、Zhiyi Yao、Fanhong Wu、Sheng Jiang

  DOI：10.1039/c2ob26556g

  日期：——

  2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling of aryl halides with various phenols under mild conditions. The catalytic system shows great functional-group tolerance and excellent reactive selectivity.

  2-Carbomethoxy-3-hydroxyquinoxaline-di- N - oxide被确定为在温和条件下铜催化芳基卤化物与各种酚偶联的有效新型配体。该催化体系显示出强大的官能团耐受性和出色的反应选择性。
• 6-(4′-Aryloxy-phenyl)vinyl-1,2,4-trioxanes: A new series of orally active peroxides effective against multidrug-resistant Plasmodium yoelii in Swiss mice
  作者：Chandan Singh、Ved Prakash Verma、Niraj Krishna Naikade、Ajit Shankar Singh、Mohammad Hassam、Sunil. K. Puri

  DOI：10.1016/j.bmcl.2010.06.045

  日期：2010.8

  A new series of 6-(4'-aryloxy-phenyl)vinyl-1,2,4-trioxanes 10a-d, 11a-d, and 12a-d have been synthesized and evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. Trioxanes 10b and 10c, the two most active compounds of the series, provided 100% protection to the infected mice at 48 mg/kg x 4 days. Clinically useful drug beta-arteether provided 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively, in this model. (C) 2010 Elsevier Ltd. All rights reserved.
• Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and S_NAr Chemistry
  作者：Kurt Polidano、Benjamin G. Reed-Berendt、Anaïs Basset、Andrew J. A. Watson、Jonathan M. J. Williams、Louis C. Morrill

  DOI：10.1021/acs.orglett.7b03441

  日期：2017.12.15

  A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice

  报道了一种通过电子芳烃活化对苯甲醇进行催化官能化的氢转移策略，该方法以优异的分离产率获得了各种定制的二芳基醚和芳基胺（38例，平均产率为70％）。利用氢转移方法，可以通过明智地选择简单和廉价的添加剂来选择功能化产物的氧化水平。