2-(2,4-dichlorophenyl)-1-(p-tolyl)ethanone | 144952-05-6

• 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: 2-(2,4-dichlorophenyl)-1-(p-tolyl)ethanone
• 英文别名: 2-(2,4-Dichlorophenyl)-1-(4-methylphenyl)ethanone
• CAS: 144952-05-6
• 化学式: C₁₅H₁₂Cl₂O
• mdl: MFCD12605220
• 分子量: 279.166
• InChiKey: HNAVOMCPFPYWLO-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C (decomp)
• 沸点：
  397.5±32.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  2-(2,4-dichlorophenyl)-1-(p-tolyl)ethanone 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 2-(2,4-dichlorophenyl)-3-(4-methylphenyl)-7-nitroimidazo[2,1-b][1,3]benzothiazole
  参考文献：
  名称：

  Synthesis and Preliminary In-Vitro Cytotoxic Activity of Novel Substituted diaryl-imidazo [2,1,b]-benzothiazole Derivatives

  摘要：

  通过2-氨基苯并噻唑衍生物（3a-g）与取代α-溴-1,2-取代二苯基-1-乙酮（7a-i）的缩合反应，合成了一系列新型取代二苯并咪唑[2,1-b]苯并噻唑衍生物（8a-y）。通过IR、1H NMR、13C NMR和质谱数据确定了合成化合物的结构。利用MTT法评估了化合物（8a-y）对小鼠（B16F10）和人（MCF-7）癌细胞的体外细胞毒活性。从体外研究中发现，化合物8p、8u和8y最为有效，对MCF-7细胞的IC50范围为0.56-27.50 μM，对B16F10细胞的IC50范围为2.57-36.54 μM。

  DOI：

  10.2174/157018011796576015
• 作为产物：
  描述：

  2,4-二氯苯乙酸 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-(2,4-dichlorophenyl)-1-(p-tolyl)ethanone
  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

• Mild, Efficient Friedel−Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl₃
  作者：Cyrous O. Kangani、Billy W. Day

  DOI：10.1021/ol800752v

  日期：2008.7.3

  A mild method for Friedel-Crafts acylation with aromatic and aliphatic carboxylic acids using cyanuric chloride, pyridine, and AlCl(3) was developed. Both inter- and intramolecular acylations were achieved at room temperature in high yield and in very short reaction times.

  开发了一种温和的方法，用于使用氰尿酰氯，吡啶和AlCl（3）与芳族和脂肪族羧酸进行Friedel-Crafts酰化。分子间和分子内的酰化反应均在室温下以高收率和很短的反应时间完成。
• Malik, Jitender K.; Noolvi, Malleshappa N.; Manvi, Fakkirappa V., Letters in drug design and discovery, 2011, vol. 8, # 9, p. 717 - 724
  作者：Malik, Jitender K.、Noolvi, Malleshappa N.、Manvi, Fakkirappa V.、Nanjwade、Patel, Harun M.、Manjula、Rao, Mallikarjuna C.、Barve, Ashutosh

  DOI：——

  日期：——
• Pd-catalyzed synthesis of α-aryl ketones through couplings of α-arylacetyl chlorides with triarylbismuths as multi-coupling nucleophiles
  作者：Maddali L.N. Rao、Somnath Giri、Deepak N. Jadhav

  DOI：10.1016/j.tetlet.2009.08.074

  日期：2009.11

  The cross-coupling reaction of alpha-arylacetyl chlorides with triarylbismuths was studied under Pd-catalyzed conditions. The reaction was found to be facile under the established protocol and furnished high yields of alpha-aryl ketones in short reaction times. This work also demonstrated a facile synthesis of various regio-isomeric mono-, di- and tri-substituted alpha-aryl ketones in high yields. Triarylbisrnuths were employed as sub-stoichiometric multi-coupling organometallic nucleophiles in this coupling protocol. (C) 2009 Elsevier Ltd. All rights reserved.
• 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
  作者：Jasia Mahdi、Haribabu Ankati、Jill Gregory、Brian Tenner、Edward R. Biehl

  DOI：10.1016/j.tetlet.2011.03.052

  日期：2011.5

  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.
• Synthesis and Preliminary In-Vitro Cytotoxic Activity of Novel Substituted diaryl-imidazo [2,1,b]-benzothiazole Derivatives
  作者：Jitender K. Malik、Malleshappa N. Noolvi、Fakkirappa V. Manvi、B.K. Nanjwade、Harun M. Patel、Manjula S. N.、Mallikarjuna Rao C.、Ashutosh Barve

  DOI：10.2174/157018011796576015

  日期：2011.10.1

  A novel series of substituted diaryl imidazo[2,1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted α-bromo-1, 2-(substituted) diaryl-1- ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56 -27.50 µ M in MCF-7 and 2.57-36.54 µ M in B16F10 cells.

  通过2-氨基苯并噻唑衍生物（3a-g）与取代α-溴-1,2-取代二苯基-1-乙酮（7a-i）的缩合反应，合成了一系列新型取代二苯并咪唑[2,1-b]苯并噻唑衍生物（8a-y）。通过IR、1H NMR、13C NMR和质谱数据确定了合成化合物的结构。利用MTT法评估了化合物（8a-y）对小鼠（B16F10）和人（MCF-7）癌细胞的体外细胞毒活性。从体外研究中发现，化合物8p、8u和8y最为有效，对MCF-7细胞的IC50范围为0.56-27.50 μM，对B16F10细胞的IC50范围为2.57-36.54 μM。