1-(4-羟基-3-甲基苯基)-3-苯基丙-2-烯-1-酮 | 2910-76-1

• 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
• 中文名称: 1-(4-羟基-3-甲基苯基)-3-苯基丙-2-烯-1-酮
• 英文名称: 4'-hydroxy-3'-methylchalcone
• 英文别名: 4'-hydroxy-3'-methyl-chalcone；4'-Hydroxy-3'-methyl-chalkon；1-(4-Hydroxy-3-methylphenyl)-3-phenylprop-2-en-1-one；1-(4-hydroxy-3-methylphenyl)-3-phenylprop-2-en-1-one
• CAS: 2910-76-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: SHPMQNTYESNIQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-(4-羟基-3-甲基苯基)-3-苯基丙-2-烯-1-酮 在 氯化亚砜 、 一水合肼 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以85%的产率得到2-methyl-4-(5'-phenyl-4,5-dihydro-1H-3-pyrazolyl)phenol
  参考文献：
  名称：

  SOCl₂ catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent ¹<i>H</i> pyrazoles

  摘要：

  一些芳基-芳基1H吡唑通过在SOCl2存在下对芳香醛和水合肼进行环化合成。吡唑的得率超过85%。这些吡唑通过其物理常数和谱学数据进行了表征。这些吡唑频率的红外和核磁共振（NMR）光谱组频率与Hammett取代基常数、F和R参数相关联。通过统计分析结果，研究了取代基对光谱频率的影响。所有合成的吡唑的抗微生物活性通过Bauer-Kirby方法进行了研究。

  DOI：

  10.4314/bcse.v28i2.11
• 作为产物：
  描述：

  2-methylphenyl cinnamate 在 四氯化钛 作用下， 反应 0.33h， 以60%的产率得到1-(4-羟基-3-甲基苯基)-3-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters

  摘要：

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。

  DOI：

  10.5012/bkcs.2011.32.1.65

文献信息

• NIR optical carbon dioxide sensors based on highly photostable dihydroxy-aza-BODIPY dyes
  作者：Susanne Schutting、Tijana Jokic、Martin Strobl、Sergey M. Borisov、Dirk de Beer、Ingo Klimant

  DOI：10.1039/c5tc00346f

  日期：——

  Optical carbon dioxide sensors based on novel self-referenced NIR colorimetric dihydroxy-aza-BODIPY dyes are presented. They possess tunable dynamic ranges and unmatched photostability.

  基于新型自参考近红外比色二羟基-氮杂BODIPY染料的光学二氧化碳传感器被提出。它们具有可调节的动态范围和无与伦比的光稳定性。
• Tautomeric origin of dual effects of N1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines on bacterial and viral strains: POM analyses as new efficient bioinformatics’ platform to predict and optimize bioactivity of drugs
  作者：Taibi Ben Hadda、Mohamed A. Ali、Vijay Masand、Said Gharby、Teffaha Fergoug、Ismail Warad

  DOI：10.1007/s00044-012-0143-6

  日期：2013.3

  In this study, we have amalgamated computational methodologies, viz. Petra, Osiris and Molinspiration (POM) to identify pharmacophores and antipharmacophores for antibacterial/antiviral activities of some 2-pyrazolines derivatives. Lipophilicity and the presence of tautomerism process are the major factors that govern the orientation to antibacterial and/or antiviral activity. On other hand, it was observed that these compounds have two different active sites and can inhibit both antiviral and antibacterial strains. Further, we have carried out receptor-based electrostatic analysis to confirm the electronic, steric and hydrophobic requirements for future modifications. The analyses provide substantial idea about the structural features responsible for their combined antibacterial/antiviral activity and provide guidelines for further modifications, with the aim of improving the activity and selectivity of designed drugs targeting HIV and tuberculosis microorganisms.The speculative assertions presented in many papers published in many reputed journals are meaningless. Most of the authors discuss of the antiviral activity compared to the antibacterial activity. There authors seem to consider that there is only one tautomeric form taking one mechanism of action for both antiviral and antibacterial activities. This is false; here, we clarify things on the basis of POM analyses.
• Neurath, Monatshefte fur Chemie, <hi>1906</hi>, vol. 27, p. 1148
  作者：Neurath

  DOI：——

  日期：——
• Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters
  作者：Jae-Ho Jeon、Deok-Mo Yang、Jong-Gab Jun

  DOI：10.5012/bkcs.2011.32.1.65

  日期：2011.1.20

  Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。
• SOCl&lt;sub&gt;2&lt;/sub&gt; catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent &lt;sup&gt;1&lt;/sup&gt;&lt;i&gt;H&lt;/i&gt; pyrazoles
  作者：K. Ranganathan、R. Suresh、G. Vanangamudi、K. Thirumurthy、P. Mayavel、G. Thirunarayanan

  DOI：10.4314/bcse.v28i2.11

  日期：——

  Some aryl-aryl 1H pyrazoles have been synthesised by cyclization of aryl chalcones and hydrazine hydrate in the presence of SOCl2. The yields of the pyrazoles are more than 85%. These pyrazoles are characterized by their physical constants and spectral data. The infrared, NMR spectral group frequencies of these pyrazolines have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the spectral frequencies have been studied. The antimicrobial activities of all synthesised pyrazolines have been studied using Bauer-Kirby method.

  一些芳基-芳基1H吡唑通过在SOCl2存在下对芳香醛和水合肼进行环化合成。吡唑的得率超过85%。这些吡唑通过其物理常数和谱学数据进行了表征。这些吡唑频率的红外和核磁共振（NMR）光谱组频率与Hammett取代基常数、F和R参数相关联。通过统计分析结果，研究了取代基对光谱频率的影响。所有合成的吡唑的抗微生物活性通过Bauer-Kirby方法进行了研究。