(2-chloro-4-nitrophenyl)(p-tolyl)methanone | 5953-01-5

• 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: (2-chloro-4-nitrophenyl)(p-tolyl)methanone
• 英文别名: 2-chloro-4-nitro-4'-metilbenzofenone；2-Chlor-4'-methyl-4-nitro-benzophenon；Cambridge id 6588495；(2-chloro-4-nitrophenyl)-(4-methylphenyl)methanone
• CAS: 5953-01-5
• 化学式: C₁₄H₁₀ClNO₃
• 分子量: 275.691
• InChiKey: DQTSJSCLYNSRNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-chloro-4-nitrophenyl)(p-tolyl)methanone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以76.1%的产率得到4-methyl-2'-chloro-4'-aminobenzophenone
  参考文献：
  名称：

  Massa; Stefancich; Artico, Farmaco, Edizione Scientifica, 1983, vol. 38, # 2, p. 90 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-4-硝基苯甲酸 在 吡啶 、 iron(III) chloride 、 三聚氯氰 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 (2-chloro-4-nitrophenyl)(p-tolyl)methanone
  参考文献：
  名称：

  Synthesis of (2-chlorophenyl)(phenyl)methanones and 2-(2-chlorophenyl)-1-phenylethanones by Friedel–Crafts acylation of 2-chlorobenzoic acids and 2-(2-chlorophenyl)acetic acids using microwave heating

  摘要：

  Several 2-(2-chlorophenyl)-1-phenylethanones and (2-chlorophenyl)(phenyl)methanones were prepared by the Friedel-Crafts acylation reaction of 2-(2-chlorophenyl) acetic acids and 2-chlorocarboxylic acids, respectively, in the presence of cyanuric chloride, pyridine, and AlCl(3) or FeCl(3) using microwave heating. The yields of the ketones were significantly higher than those obtained using conventional heating. In addition, similar reactions carried out with the less inexpensive and less toxic FeCl(3) gave titled ketones in comparable yields. Interestingly, the FeCl(3) catalyzed reactions gave pure ketones (no chromatographic purification required), whereas the AlCl(3) catalyzed reaction gave impure product that required chromatographic purification. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.052

文献信息

• Aerobic oxidative acylation of nitroarenes with arylacetic esters under mild conditions: facile access to diarylketones
  作者：Jiang-Sheng Li、Qian Yang、Fan Yang、Guo-Qin Chen、Zhi-Wei Li、Yin-Jie Kuang、Wei-Jing Zhang、Peng-Mian Huang

  DOI：10.1039/c7ob02865b

  日期：——

  A facile and regioselective base-mediated aerobic oxidative acylation of nitroarenes to access diarylketones under mild conditions has been developed. It features the use of bench-stable and readily available arylacetates as acyl surrogates, and the absence of transition-metals and synthetic oxidants. This protocol involves a cascade CDC/oxidative decarboxylation process.

  已经开发了在温和条件下容易和区域选择性的碱介导的硝基芳烃的好氧氧化酰化，以得到二芳基酮。它具有使用稳定的，易于获得的芳基乙酸酯作为酰基替代物的特点，并且不存在过渡金属和合成氧化剂。该方案涉及级联的CDC /氧化脱羧过程。
• Pagliarini; Cignarella; Testa, Farmaco, Edizione Scientifica, 1965, vol. 20, # 10, p. 686 - 695
  作者：Pagliarini、Cignarella、Testa

  DOI：——

  日期：——
• MASSA, S.;STEFANCICH, G.;ARTICO, M.;CORELLI, F.;BAGLIONI, A.;ANGELUCCI, L+, FARMACO. ED. SCI., 1983, 38, N 2, 90-100
  作者：MASSA, S.、STEFANCICH, G.、ARTICO, M.、CORELLI, F.、BAGLIONI, A.、ANGELUCCI, L+

  DOI：——

  日期：——