8-cinnamoyl-7-hydroxy-4-methyl-2H-chromen-2-one | 115664-84-1

• 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
• 英文名称: 8-cinnamoyl-7-hydroxy-4-methyl-2H-chromen-2-one
• 英文别名: 7-hydroxy-4-methyl-8-[(E)-3-phenylprop-2-enoyl]chromen-2-one
• CAS: 115664-84-1
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: MFNVQLMPJMITCT-VQHVLOKHSA-N

物化性质

• 熔点：
  160 °C(Solv: methanol (67-56-1))
• 沸点：
  568.1±50.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-cinnamoyl-7-hydroxy-4-methyl-2H-chromen-2-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.57h， 以80%的产率得到4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-one
  参考文献：
  名称：

  Microwave-assisted synthesis of substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones and their antimicrobial activity

  摘要：

  Chromene and coumarin scaffolds are known for their potential antimicrobial activity. Herein, we have synthesized hybrid compounds containing both, substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones, 3a-o have been synthesized from substituted (E)-1-(7-Hydroxy-4-methyl-8-coumarinyl)-3-phenyl-2-propen-1-ones, 2a-o in good yield using the microwave-assisted Vilsmeier-Haack reaction. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 3e, 3f and 3g were found to be potent against tested fungal and bacterial strains.

  DOI：

  10.1007/s00044-014-1204-9
• 作为产物：
  描述：

  8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 、 苯甲醛 在 哌啶 作用下， 生成 8-cinnamoyl-7-hydroxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Microwave-assisted synthesis of (E)-7-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]-8-(3-arylacryloyl)-4-methyl-2H-chromen-2-ones and their antimicrobial activity

  摘要：

  混合化合物是结构活性关系分析中相关的产品。合成了一系列含有香豆素、1,2,3-三唑和香豜素亚结构的混合化合物，并对它们的抗菌活性进行了筛选。合成化合物的结构已根据分析和光谱数据确定。

  DOI：

  10.1515/hc-2014-0102

文献信息

• Microwave-assisted synthesis of (<i>E</i>)-7-[(1-benzyl-1<i>H</i>-1,2,3-triazol-4-yl)methoxy]-8-(3-arylacryloyl)-4-methyl-2<i>H</i>-chromen-2-ones and their antimicrobial activity
  作者：Ashok Dongamanti、Vijaya Lakshmi Bommidi、Ganesh Arram、Ravi Sidda

  DOI：10.1515/hc-2014-0102

  日期：2014.10.1

  Hybrid compounds are relevant products in the structure-activity relationships analysis. A new series of hybrid compounds containing coumarin, 1,2,3-triazole, and chalcone substructures were synthesized and screened for their antimicrobial activity. The structures of the synthesized compounds have been established on the basis of analytical and spectral data.

  混合化合物是结构活性关系分析中相关的产品。合成了一系列含有香豆素、1,2,3-三唑和香豜素亚结构的混合化合物，并对它们的抗菌活性进行了筛选。合成化合物的结构已根据分析和光谱数据确定。

• Sangwan, Naresh K.; Verma, Braham S.; Dhindsa, Kuldip Singh, Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 1, p. 137 - 141
  作者：Sangwan, Naresh K.、Verma, Braham S.、Dhindsa, Kuldip Singh

  DOI：——

  日期：——
• SANGWAN, NARESH K.;VERMA, BRAHAM S.;DHINDSA, KULDIP SINGH, J. PRAKT. CHEM., 330,(1988) N 1, 137-141
  作者：SANGWAN, NARESH K.、VERMA, BRAHAM S.、DHINDSA, KULDIP SINGH

  DOI：——

  日期：——
• Microwave-assisted synthesis of substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones and their antimicrobial activity
  作者：D. Ashok、B. Vijaya Lakshmi、S. Ravi、A. Ganesh

  DOI：10.1007/s00044-014-1204-9

  日期：2015.4

  Chromene and coumarin scaffolds are known for their potential antimicrobial activity. Herein, we have synthesized hybrid compounds containing both, substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones, 3a-o have been synthesized from substituted (E)-1-(7-Hydroxy-4-methyl-8-coumarinyl)-3-phenyl-2-propen-1-ones, 2a-o in good yield using the microwave-assisted Vilsmeier-Haack reaction. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 3e, 3f and 3g were found to be potent against tested fungal and bacterial strains.