1-(2-hydroxy-phenyl)-3-p-tolyl-propan-1-one | 6619-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxy-phenyl)-3-p-tolyl-propan-1-one
• 英文别名: 3-(4-methylphenyl)-1-(2-hydroxyphenyl)propan-1-one；1-(2-hydroxyphenyl)-3-(4-methylphenyl)propan-1-one；2'-Hydroxy-4-methyl-ω-benzylacetophenon
• CAS: 6619-28-9
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ZENLLPKFNHYMQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-phenyl)-3-p-tolyl-propan-1-one 在 sodium hydroxide 作用下， 反应 13.0h， 生成 1-[2-[2-Hydroxy-3-(propylamino)propoxy]phenyl]-3-(4-methylphenyl)propan-1-one
  参考文献：
  名称：

  Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study

  摘要：

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.013
• 作为产物：
  描述：

  1-(2-羟基苯基)-3-(4-甲基苯基)-2-丙烯-1-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以89%的产率得到1-(2-hydroxy-phenyl)-3-p-tolyl-propan-1-one
  参考文献：
  名称：

  溶剂控制的2'-羟基查耳酮的氢化反应：简单合成Bussealins的简单方法

  摘要：

  本文报道了溶剂控制的2'-羟基查耳酮氢化，以选择性地获得不同的氢化产物。因此，使用EtOH作为溶剂对2'-羟基查耳酮进行氢化，可以以优异的产率提供相应的1,3-二芳基丙烷。相反，当在DCM中进行氢化时，分离出相应的二氢查耳酮。将反应溶剂切换为n- BuOH / H 2 O（1：1），得到1,3-二芳基丙醇，产率从中等到良好。此处报道的方法为制备各种2'-羟基-1,3-二芳基丙烷衍生物提供了一种简单，简单且具有成本效益的方法，并且还应用于天然Bussealins C和D的制备。

  DOI：

  10.1002/adsc.202000892

文献信息

• Synthesis and structural characterization of facile ruthenium(II) hydrazone complexes: Efficient catalysts in α-alkylation of ketones with primary alcohols via hydrogen auto transfer
  作者：Subbarayan Vijayapritha、Kaliyappan Murugan、Periasamy Viswanathamurthi、Paranthaman Vijayan、Chinnasamy Kalaiarasi

  DOI：10.1016/j.ica.2020.119887

  日期：2020.11

  successfully applied as catalysts in α -alkylation of aliphatic and aromatic ketones with alcohols via borrowing hydrogen strategy. Various parameters such as base, solvent, temperature, time and catalyst loading on the catalytic activity were analyzed. From the results, the catalyst 1 was found to be the best catalyst for α-alkylation reaction to obtain excellent yield. The catalytic system has a broad

  摘要为了开发新的配合物，新的Ru（II）配合物（1-3）由[Ru（SAL-HBT）（CO）（AsPh3）2]，[Ru（VAN） -HBT）（CO）（AsPh3）2]和[Ru（NAP-HBT）（CO）Cl（AsPh3）2] [SAL-HBT =（水杨基（（2-（苯并噻唑-2基）肼基）甲基苯酚））， VAN-HBT = 2-（（（2-（苯并噻唑-2-基）肼基）甲基）-6甲氧基苯酚）和NAP-HBT =萘基-2-（（2-（苯并噻唑-2-基）肼基）甲基苯酚）合成。通过令人满意的元素分析，各种光谱技术（IR，（1H，13C）NMR）以及质谱法确定了它们的身份。钌（II）离子具有扭曲的八面体几何形状的六配位体。在配合物1和2中，配体通过形成N 1 N供体5元和N 2 O供体6元螯合环而以双阴离子三齿形式配位。然而，在配合物3中，配体通过形成N 1 N供体五元环以单阴离子二齿形式配位。新的钌（II）羰基
• Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives
  作者：Lalitha Simon、Abdul Ajees Abdul Salam、S. Madan Kumar、T. Shilpa、K.K. Srinivasan、K. Byrappa

  DOI：10.1016/j.bmcl.2017.10.026

  日期：2017.12

  exhibited moderate activity against HeLa cells (IC50 = 42.8 µM). The molecular structures of 3h and 3i were solved by single crystal X-ray crystallographic technique. Additionally, the molecular docking studies between the tumour suppressor protein p53 with the lead compound 3h, which exhibited better anticancer activity against HeLa cells was examined.

  合成了一系列的3-苄基苯并吡喃-4-酮，并通过MTT法筛选了其抗癌活性。针对两种癌细胞系BT549（人类乳腺癌），HeLa（人类宫颈癌）和一种非癌细胞系vero（正常肾脏上皮细胞）对化合物进行了评估。发现3b是对抗BT549细胞（IC 50  = 20.1 µM）最活跃的分子，而3h是对抗HeLa细胞（IC 50  = 20.45 µM）最活跃的分子。3b还显示出对HeLa细胞的中等活性（IC 50  = 42.8 µM）。3h和3i的分子结构通过单晶X射线晶体学技术解决。此外，检查了在肿瘤抑制蛋白p53与先导化合物3h之间的分子对接研究，该化合物对HeLa细胞表现出更好的抗癌活性。
• Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis
  作者：Sofiya A. Runikhina、Alexey A. Tsygankov、Oleg I. Afanasyev、Denis Chusov

  DOI：10.1016/j.mencom.2023.01.005

  日期：2023.1

  Fluoride additive to [(p-cymene)RuCl2]2, a readily available ruthenium catalyst, allows one to achieve milder conditions for the reductive alkylation of aldehydes with ketones using carbon monoxide as a reducing agent. The procedure is suitable for the broad substrate scope, and a probable explanation for the fluoride role was provided.

  [(对伞花烃) RuCl 2 ] 2的氟化物添加剂，一种现成的钌催化剂，允许人们使用一氧化碳作为还原剂实现醛与酮的还原性烷基化。该程序适用于广泛的底物范围，并提供了对氟化物作用的可能解释。
• Synthesis of 3 -methylbenzyl ? 4 -hydroxycoumarins, and their hydrolysis
  作者：M. P. Aleksyuk、A. I. Shcherban、L. P. Zalukaev

  DOI：10.1007/bf00480952

  日期：——