1-(4-chlorophenyl)-2-(naphthalen-2-yl)ethane-1, 2-dione | 1313850-20-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-chlorophenyl)-2-(naphthalen-2-yl)ethane-1, 2-dione
• 英文别名: 1-(4-Chlorophenyl)-2-naphthalen-2-ylethane-1,2-dione；1-(4-chlorophenyl)-2-naphthalen-2-ylethane-1,2-dione
• CAS: 1313850-20-2
• 化学式: C₁₈H₁₁ClO₂
• 分子量: 294.737
• InChiKey: NFQKDCWYJOYRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-(naphthalen-2-yl)ethane-1, 2-dione 在 硫酸 、 sulfur 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 生成 2-(4-chlorophenyl)-3-(2-naphthyl)pyrazine
  参考文献：
  名称：

  One-pot synthesis of unsymmetrical benzils and N-heteroarenes through nucleophilic aroylation catalyzed by N-heterocyclic carbene

  摘要：

  An efficient one-pot synthesis of various unsymmetrical benzils via N-heterocyclic carbene (NHC)-catalyzed aroylation of N-phenylimidoyl chlorides with aromatic aldehydes followed by acidic hydrolysis has been developed. The one-pot procedure was extended to synthesis of quinoxalines and pyrazines by condensation/annulation of unsymmetrical benzils generated in situ with diamines. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.039
• 作为产物：
  描述：

  p-Chlorbenzyl-β-naphthylketon 在 氧气 、 copper diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以102 mg的产率得到1-(4-chlorophenyl)-2-(naphthalen-2-yl)ethane-1, 2-dione
  参考文献：
  名称：

  芳基三氟硼酸钾加氧到（杂）芳基乙腈中的两步一锅合成不对称（杂）芳基1,2-二酮

  摘要：

  已经开发了一种有效的两步一锅法，用于合成不对称的（杂）芳基1,2-二酮。反应通过芳族三氟硼酸钾的钯催化亲核加成反应到脂肪族腈中，然后使用分子氧作为绿色氧化剂，进行铜催化的需氧苄基CH氧化。

  DOI：

  10.1002/ejoc.201701625

文献信息

• Synthesis of unsymmetrical benzils using N-heterocyclic carbene catalysis
  作者：Yumiko Suzuki、Abu Bakar、Takashi Tanoi、Naoko Nomura、Masayuki Sato

  DOI：10.1016/j.tet.2011.04.020

  日期：2011.6

  In this paper, we propose a novel and efficient method for the preparation of various unsymmetrical benzils. We first demonstrate the nucleophilic aroylation of N-phenylbenzimidoyl chlorides with aromatic aldehydes using N-heterocyclic carbene as the catalyst to afford 1-aryl-2-phenyl-2-(phenylimino)ethanones. These iminoethanones were then converted to 1,2-diaryl-1,2-diketones by acid-promoted hydrolysis

  在本文中，我们提出了一种新颖而有效的方法来制备各种不对称的苯甲。我们首先证明了N-苯基苯甲酰亚胺基氯与芳香醛的亲核芳基化反应，使用N-杂环卡宾作为催化剂，得到了1-芳基-2-苯基-2-（苯基亚氨基）乙炔。然后通过酸促进的水解将这些亚氨基乙基酮转化为1,2-二芳基-1,2-二酮。
• Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
  作者：Yogesh Kumar、Yogesh Jaiswal、Amit Kumar

  DOI：10.1002/ejoc.201701625

  日期：2018.1.31

  An efficient two‐step one‐pot procedure for the synthesis of unsymmetrical (hetero)aryl 1,2‐diketones has been developed. The reaction proceeds through a palladium‐catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper‐catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant.

  已经开发了一种有效的两步一锅法，用于合成不对称的（杂）芳基1,2-二酮。反应通过芳族三氟硼酸钾的钯催化亲核加成反应到脂肪族腈中，然后使用分子氧作为绿色氧化剂，进行铜催化的需氧苄基CH氧化。
• One-pot synthesis of unsymmetrical benzils and N-heteroarenes through nucleophilic aroylation catalyzed by N-heterocyclic carbene
  作者：Yumiko Suzuki、Mai Murofushi、Kei Manabe

  DOI：10.1016/j.tet.2012.11.039

  日期：2013.1

  An efficient one-pot synthesis of various unsymmetrical benzils via N-heterocyclic carbene (NHC)-catalyzed aroylation of N-phenylimidoyl chlorides with aromatic aldehydes followed by acidic hydrolysis has been developed. The one-pot procedure was extended to synthesis of quinoxalines and pyrazines by condensation/annulation of unsymmetrical benzils generated in situ with diamines. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.