2-(2-chloro-4-fluorophenyl)-1-(2-hydroxy-3-methylphenyl)ethanone | 1598413-18-3

• 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-chloro-4-fluorophenyl)-1-(2-hydroxy-3-methylphenyl)ethanone
• 英文别名: 2-(2-Chloro-4-fluorophenyl)-1-(2-hydroxy-3-methylphenyl)ethanone
• CAS: 1598413-18-3
• 化学式: C₁₅H₁₂ClFO₂
• 分子量: 278.71
• InChiKey: ZCCBPXFFCTYMOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chloro-4-fluorophenyl)-1-(2-hydroxy-3-methylphenyl)ethanone 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 甘油 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives

  摘要：

  This paper describes the synthesis and the antiproliferative activities of compounds 9a-r, 3-aryl analogs of flavone-8-acetic acid that bear diverse substituents on the benzene rings at the 2- and 3-positions of the flavone nucleus. Their direct and indirect cytotoxicities were evaluated against HT-29 human colon adenocarcinoma cell lines, A549 lung adenocarcinoma cell lines and Human Peripheral Blood Mononuclear Cells (HPBMCs). The results indicate that most of the compounds bearing electron-withdrawing substituents (9b-m) exhibited moderate direct cytotoxicities. And compounds 9e and 9i showed comparable indirect cytotoxicities with 5, 6-dimethylxanthenone-4-acetic acid (DMXAA), and low direct cytotoxicities toward HPBMCs. Interestingly, the compounds 9n-r bearing methoxy groups at the 2- or 3-position of the flavone nucleus exhibited higher indirect cytotoxicities against A549 cell lines than DMXAA, and lower cytotoxicities against HPBMCs. In addition, compounds 9p-r were found to be able to induce tumor necrosis factor alpha (TNF-alpha) production in HPBMCs. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.030
• 作为产物：
  描述：

  在 caesium carbonate 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 6.17h， 生成 2-(2-chloro-4-fluorophenyl)-1-(2-hydroxy-3-methylphenyl)ethanone
  参考文献：
  名称：

  微波辅助有效地从水中易制得的3-芳基-4-羟基香豆素碱分解法合成2-羟基脱氧安息香素。

  摘要：

  本文描述了一种操作简单，绿色高效的方法，该方法可通过微波辅助的3-芳基-4-羟基香豆素在水中的碱降解来合成带有各种取代基的2-羟基脱氧安息香素。后者的化合物很容易从2-（2-芳基乙酰氧基）苯甲酸甲酯的分子内克莱森缩合反应中，在Cs2CO3-丙酮存在下，以极好的收率和费力的后处理步骤制备。该方法是高度原子经济的，因此可用于大规模合成2-羟基脱氧苯偶姻。

  DOI：

  10.1248/cpb.c13-00604

文献信息

• Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives
  作者：Guang-Hua Yan、Xiao-Fang Li、Bing-Chen Ge、Xiu-Dong Shi、Yu-Fang Chen、Xue-Mei Yang、Jiang-Ping Xu、Shu-Wen Liu、Pei-Liang Zhao、Zhong-Zhen Zhou、Chun-Qiong Zhou、Wen-Hua Chen

  DOI：10.1016/j.ejmech.2014.11.030

  日期：2015.1

  This paper describes the synthesis and the antiproliferative activities of compounds 9a-r, 3-aryl analogs of flavone-8-acetic acid that bear diverse substituents on the benzene rings at the 2- and 3-positions of the flavone nucleus. Their direct and indirect cytotoxicities were evaluated against HT-29 human colon adenocarcinoma cell lines, A549 lung adenocarcinoma cell lines and Human Peripheral Blood Mononuclear Cells (HPBMCs). The results indicate that most of the compounds bearing electron-withdrawing substituents (9b-m) exhibited moderate direct cytotoxicities. And compounds 9e and 9i showed comparable indirect cytotoxicities with 5, 6-dimethylxanthenone-4-acetic acid (DMXAA), and low direct cytotoxicities toward HPBMCs. Interestingly, the compounds 9n-r bearing methoxy groups at the 2- or 3-position of the flavone nucleus exhibited higher indirect cytotoxicities against A549 cell lines than DMXAA, and lower cytotoxicities against HPBMCs. In addition, compounds 9p-r were found to be able to induce tumor necrosis factor alpha (TNF-alpha) production in HPBMCs. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Microwave-Assisted Efficient Synthesis of 2-Hydroxydeoxybenzoins from the Alkali Degradation of Readily Prepared 3-Aryl-4-hydroxycoumarins in Water
  作者：Zhong-Zhen Zhou、Guang-Hua Yan、Wen-Hua Chen、Xue-Mei Yang

  DOI：10.1248/cpb.c13-00604

  日期：——

  This paper describes an operationally simple, green and efficient approach for the synthesis of 2-hydroxydeoxybenzoins bearing diverse substituents from the microwave-assisted alkali degradation of 3-aryl-4-hydroxycoumarins in water. The latter compounds were readily prepared from the intramolecular Claisen condensation reaction of methyl 2-(2-arylacetoxy)benzoates in the presence of Cs2CO3-acetone

  本文描述了一种操作简单，绿色高效的方法，该方法可通过微波辅助的3-芳基-4-羟基香豆素在水中的碱降解来合成带有各种取代基的2-羟基脱氧安息香素。后者的化合物很容易从2-（2-芳基乙酰氧基）苯甲酸甲酯的分子内克莱森缩合反应中，在Cs2CO3-丙酮存在下，以极好的收率和费力的后处理步骤制备。该方法是高度原子经济的，因此可用于大规模合成2-羟基脱氧苯偶姻。