6-acetyl-7-hydroxy-2,2-dimethylchroman-4-one | 122587-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-acetyl-7-hydroxy-2,2-dimethylchroman-4-one
• 英文别名: 6-acetyl-7-hydroxy-2,2-dimethyl-3H-chromen-4-one
• CAS: 122587-27-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: MGEIZTZOFFEBNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±45.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-acetyl-7-hydroxy-2,2-dimethylchroman-4-one 在 盐酸 、 sodium tetrahydroborate 、 羟胺 、 sodium acetate 、 乙酸酐 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 3,7,7-trimethyl-7H-pyrano<3,2-f>-1,2-benzisoxazole
  参考文献：
  名称：

  Heterocycles from Diacetyl Phenols: Synthesis of Benzodioyrans, Acetylchromenes and Pyrano[1,2]benzisoxazoles

  摘要：

  DOI：

  10.3987/com-88-s135
• 作为产物：
  描述：

  1-(5-Acetyl-2,4-dihydroxyphenyl)-3-hydroxy-3-methylbutan-1-one 在 六甲基磷酰三胺 作用下， 以91%的产率得到6-acetyl-7-hydroxy-2,2-dimethylchroman-4-one
  参考文献：
  名称：

  Heterocycles from Diacetyl Phenols: Synthesis of Benzodioyrans, Acetylchromenes and Pyrano[1,2]benzisoxazoles

  摘要：

  DOI：

  10.3987/com-88-s135

文献信息

• Solvent-free microwave-assisted synthesis and biological evaluation of aurones and flavanones based on 2,2-dimethylchroman-4-one
  作者：Dongamanti Ashok、Rayagiri Suneel Kumar、Devulapally Mohan Gandhi、Anireddy Jayashree

  DOI：10.1007/s10593-016-1917-4

  日期：2016.7

  A series of novel 8-aryl-2,2-dimethyl-2,3,7,8-tetrahydropyrano[3,2-g]chromene-4,6-dione and 2-arylidene-7,7-dimethyl-6,7-dihydro-2H-furo[3,2-g]chromene-3,5-dione derivatives have been synthesized by oxidation of the corresponding chalcones under microwave irradiation. All newly synthesized compounds were characterized by IR, 1H, 13C NMR, and mass spectra and valuated for their in vitro antibacterial

  一系列新颖的8-芳基-2,2-二甲基-2,3,7,8-四氢吡喃[3,2 - g ]色烯-4,6-二酮和2-亚芳基-7,7-二甲基-6，通过在微波辐射下氧化相应的查耳酮，已经合成了7-二氢-2 H-呋喃[3,2-g]亚甲基-3,5-二酮衍生物。所有新合成的化合物均通过IR，1 H，13 C NMR和质谱进行表征，并对其体外抗菌和抗真菌活性进行了评估。
• Solvent-free microwave-assisted synthesis and biological evaluation of 2,2-dimethylchroman-4-one based benzofurans
  作者：Dongamanti Ashok、Rayagiri Suneel Kumar、Devulapally Mohan Gandhi、Madderla Sarasija、Anireddy Jayashree、Shaik Adam

  DOI：10.1515/hc-2016-0147

  日期：2016.12.1

  A series of novel chroman-4-one fused benzofurans were synthesized by cyclization of the corresponding chalcones under microwave irradiation. All new compounds were characterized by IR, ¹H NMR, ¹³C NMR and mass spectral data and were evaluated for their in vitro antimicrobial and antioxidant activities.

  摘要 通过在微波辐射下合成相应的查尔酮，合成了一系列新颖的嵌合苯并呋喃类色素-4-酮。所有新化合物均通过红外光谱、1H核磁共振、13C核磁共振和质谱数据进行表征，并评估其体外抗微生物和抗氧化活性。
• Photochemistry of 7-acetoxybenzopyran derivatives. Synthesis of eupatoriochromene and encecalin
  作者：Miguel A. Miranda、Jaime Primo、Rosa Tormos

  DOI：10.1016/s0040-4020(01)89221-8

  日期：1989.1

  The photolysis of the 7-acetoxybenzopyran derivatives 1a-5a has been carried out. Chromene 1a was found to undergo extensive photopolymerization. Chromanone 2a underwent a rather inefficient photo-Fries rearrangement to the 6 - and 8 - acetyl derivatives 2b and 2c. Diacetoxychromene 3a gave the unsaturated ketone 8 as the main product, besides its deacetylation analogue 9 and chromanone 11. Diacetoxychroman

  7-乙酰氧基苯并吡喃衍生物1a-5a的光解已经进行。发现Chromene 1a进行了广泛的光聚合。Chromanone 2a经历了效率低下的Photo-Fries重排反应，生成6-和8-乙酰基衍生物2b和2c。Diacetoxychromene图3a，得到不饱和酮8作为主要产物，除了它的脱乙酰化类似物9和二氢吡喃酮11。二乙酰氧基铬烷4a提供了四种C-乙酰基产物的混合物：1b，1c，2b和2c，以及Chromene 1a和苯并二氢吡喃酮2a。最后，苯并二氢吡喃5a的辐射产生了两种可能的光炸产物5b（43％）和5c（52％）的混合物。讨论了以上结果的机理意义，特别强调了与吡喃环，烯醇酯和苄基酯部分相比，苯酯的光反应性。这些转化的合成应用通过制备紫杉烯酮1b和encecalin 1e进行了说明。
• Synthesis of novel 2,4,6-trisubstituted pyrimidine derivatives and their in vitro antimicrobial activity
  作者：D. Ashok、R. Suneel Kumar、D. Mohan Gandhi、A. Jayashree

  DOI：10.1134/s1070363216060268

  日期：2016.6

  A series of novel pyrimidines (6a-6i) has been synthesized from corresponding chalcones and isonicotinimidamide.HCl in the presence of potassium carbonate involving Michael addition followed by cycloaddition. All newly synthesised chalcones and pyrimidines were screened for in vitro antimicrobial activity against various Gram positive, Gram negative bacterial and fungal strains. Most of compounds displayed high antimicrobial activity compared to standard drugs Penicillin, Streptomycin and Ampothericin-B.
• Banerji, A.; Kalena, G.P., Synthetic Communications, 1989, vol. 19, # 1, 2, p. 159 - 166
  作者：Banerji, A.、Kalena, G.P.

  DOI：——

  日期：——