(E)-1-(5-chloro-2-hydroxy-4-methylphenyl)-3-phenylprop-2-en-1-one | 41011-08-9

• 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: (E)-1-(5-chloro-2-hydroxy-4-methylphenyl)-3-phenylprop-2-en-1-one
• 英文别名: 5'-chloro-2'-hydroxy-4'-methyl-trans-chalcone；5'-Chlor-2'-hydroxy-4'-methyl-trans-chalkon；5'-Chloro-2'-hydroxy-4'-methylchalcone
• CAS: 41011-08-9
• 化学式: C₁₆H₁₃ClO₂
• 分子量: 272.731
• InChiKey: LXIAAMCDAHDXEY-BQYQJAHWSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-1-(5-chloro-2-hydroxy-4-methylphenyl)-3-phenylprop-2-en-1-one 以 苯 为溶剂， 反应 8.0h， 以48%的产率得到6-Chloro-7-methyl-2-phenyl-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Kamboj, Ramesh C.; Berar, Surinder; Berar, Urmila, Journal of the Indian Chemical Society, 2011, vol. 88, # 6, p. 879 - 885

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铝 、 硝基苯 作用下， 生成 (E)-1-(5-chloro-2-hydroxy-4-methylphenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Christian; Amin, Journal of the Indian Chemical Society, 1959, vol. 36, p. 715,718

  摘要：

  DOI：

文献信息

• 6-Chloro-7-methyl-3', 4'-dimethoxyflavone – a Potent Selective COX-2 Inhibitor
  作者：Rafia Bashir、Kalim Javed、Shafiya Yaseen、Syed Ovais、Pooja Rathore、Hinna Hamid、M. S. Alam、Mohammed Samim、Surender Singh、Vinod Nair

  DOI：10.2174/1573406411309040016

  日期：2013.4.1

  Some unnatural chalcones (1a-q) and flavones (2a-d) have been synthesized and evaluated for their antiinflammatory activity using carrageenan-induced rat paw edema assay. The flavone 2c (6-Chloro-7-methyl-3', 4'- dimethoxyflavone) had higher anti-inflammatory activity and superior gastrointestinal safety profiles than the reference drug celecoxib. Compound 2c showed almost two times better selective inhibitory activity towards COX-2 enzyme than celecoxib. 2'-Hydroxychalcones (1a-h) showed moderate to strong anti-inflammatory activity (38.6-82.4 % at 3h and 52.4–80.2 % at 5h). Among 2'-methoxychalcones (1i-q) 1k and 1q exhibited maximum activity 82.6% (at 3h) and 84.3% (at 5h) respectively.

  合成了一些非天然的查尔酮（1a-q）和黄酮（2a-d），并通过卡拉胶诱导的大鼠足部水肿实验评估了它们的抗炎活性。黄酮2c（6-氯-7-甲基-3', 4'-二甲氧基黄酮）具有比参考药物塞来昔布更高的抗炎活性和更优的胃肠安全性。化合物2c对COX-2酶的选择性抑制活性几乎是塞来昔布的两倍。2'-羟基查尔酮（1a-h）显示出中等到强的抗炎活性（在3小时时为38.6-82.4%，在5小时时为52.4–80.2%）。在2'-美氧基查尔酮（1i-q）中，化合物1k和1q分别显示出最高的活性，3小时时为82.6%，5小时时为84.3%。
• Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization
  作者：Zachary D. Miller、Byung Joo Lee、Tehshik P. Yoon

  DOI：10.1002/anie.201706975

  日期：2017.9.18

  Cross-products: Lewis acid catalyzed triplet sensitization enables the highly enantioselective crossed cycloaddition of chalcones and styrenes to forge cyclobutane cores. These cores are found in multiple bioactive natural products.

  交叉产物：路易斯酸催化的三重态敏化作用使查尔酮和苯乙烯具有高度对映选择性的交叉环加成反应，从而形成环丁烷核。这些核心存在于多种生物活性天然产物中。
• Synthesis of Flavones through NaI‐Mediated Electrochemical Cyclization of Chalcones
  作者：Taweesak Gulchatchai、Thao Nguyen Thanh Huynh、Natthanan Vijara、Tanatorn Khotavivattana、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1002/ejoc.202300556

  日期：2023.9.21

  In this work, we demonstrated a novel electrochemical oxidative cyclization for synthesis of flavone from 2’-hydroxychalcone using an inexpensive using low toxic NaI as mediator/electrolyte without external additives in EtOH/water solvent. The key features of this reaction include its broad substrate scope, scalability, ability to operate with benign solvent at room temperature, and no requirement

  在这项工作中，我们展示了一种新型电化学氧化环化方法，用于从 2'-羟基查耳酮合成黄酮，使用廉价的低毒 NaI 作为介体/电解质，无需外部添加剂，在乙醇/水溶剂中。该反应的主要特点包括底物范围广泛、可扩展性、能够在室温下使用良性溶剂进行操作，并且不需要强氧化剂和外部添加剂。
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
• ESTROGEN RECEPTOR ALPHA COLIGANDS, AND METHODS OF USE THEREOF
  申请人：The Regents of the University of California

  公开号：US20190008797A1

  公开（公告）日：2019-01-10

  Provided herein is a coligand for the estrogen receptor (ER) a subunit, and methods of use thereof in treating conditions associated with ER signaling in an individual. The present ERα coligand may be a cell type-selective, allosteric modulator of ERα signaling. The ERα coligand, when administered to an individual, may modulate ER agonist-dependent signaling in a tissue-selective manner.