3-methyl-4H-naphtho[2,1-b]pyran-1-one | 5891-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-methyl-4H-naphtho[2,1-b]pyran-1-one
• 英文别名: 3-methyl-1H-naphtho<2,1-b>pyran-1-one；3-methyl-1H-benzo[f]chromen-1-one；2-methyl-5,6-benzochromone；3-methyl-benzo[f]chromen-1-one；3-Methyl-benzo[f]chromen-1-on；2-Methyl-5.6-benzo-chromon；3-Methyl-1H-naphtho[2,1-b]pyran-1-one；3-methylbenzo[f]chromen-1-one
• CAS: 5891-82-7
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: SABIKCKVFBNFFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-4H-naphtho[2,1-b]pyran-1-one 在 吡啶 、 盐酸羟胺 作用下， 以 水 为溶剂， 反应 4.0h， 生成 1-(5-methyl-isoxazol-3-yl)-naphthalen-2-ol
  参考文献：
  名称：

  Sammour,A. et al., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 271 - 280

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-1-naphthoylacetone 在 硫酸 作用下， 生成 3-methyl-4H-naphtho[2,1-b]pyran-1-one
  参考文献：
  名称：

  Infrared spectra and theoretical study of methyl, formyl and acetyl derivatives of chromones

  摘要：

  The C=O stretching frequencies of substituted 2-methylchromones (3a-3j). 2-formylchromones (4a-4j), 3-formylchromones (5a-5j) and 3-acetyl-2-methylchromones (6a-6i) were measured in CCl4 and CHCl3 and correlated with sigma+ substituent constants. Using the results of the infrared spectral investigation and the theoretical calculations by the semiempirical AM1 method, the conformation and the transmission of electronic effects in compounds 4-6 were studied. For the 2-substituted chromone system the transmission factory gamma according to the definition of Charton was determined. The preparation of some new 2-methylchromones (3e-3j) and 3-(2,2-diformyl-chlorovinyl)-6-methylchromone (7) is also described.

  DOI：

  10.1007/bf00819522

文献信息

• A Novel and Efficient Synthetic Method of Benzo[<i>f</i>]chromen-1-ones and Phenyl-4<i>H</i>-chromen-4-one through Photooxidative Cyclization of 6-[(<i>E</i>)-2-Arylvinyl]-4<i>H</i>-pyran-4-ones and 6-[(1<i>E</i>,3E)-4-Phenylbuta-1,3-dien-1-yl]-4<i>H</i>-pyran-4-one
  作者：Nabila Aït-Baziz、Safouane M. Hamdi、Artur M. S. Silva、Yahia Rachedi、Maamar Hamdi、Mohamed Trari

  DOI：10.1002/jhet.1694

  日期：2014.9

  A rapid and efficient microwave‐assisted transformation of 2‐pyrones into 4‐pyrones is reported. Then, a new photocatalytic oxidative cyclization of 6‐[(E)‐2‐arylvinyl]‐2‐methyl‐4H‐pyran‐4‐ones and 2‐methyl‐6‐[(1E,3E)‐4‐phenylbuta‐1,3‐dien‐1‐yl]‐4H‐pyran‐4‐one with UV light in the presence of a catalytic amount of CuAlO2 is described. We obtained new 3‐methyl‐1H‐benzo[f]chromen‐1‐ones and 2‐methyl

  据报道，微波辅助快速有效地将2吡喃酮转化为4吡喃酮。然后，对6-[（（E）-2-芳基乙烯基] -2-甲基-4 H-吡喃-4-酮和2-甲基-6-[（1 E，3 E）-4- ]进行新的光催化氧化环化描述了在催化量的CuAlO 2的存在下，用紫外线在苯基丁1，3，dien-1，1基] -4 H，吡喃-4-1 。我们获得了新的3-甲基-1 H-苯并[ f ]铬n-1-酮和2-甲基-5-苯基-4 H-铬n-4-酮，它们已通过光谱技术进行了充分表征。
• Tandem Reactions Leading to Bicyclic Pyrimidine Nucleosides and Benzopyran-4-ones
  作者：Xuesen Fan、Yangyang Wang,、Yingying Qu、Haiyun Xu、Yan He、Xinying Zhang、Jianji Wang

  DOI：10.1021/jo102131y

  日期：2011.2.4

  and efficient synthesis of bicyclic pyrimidine nucleosides and benzopyran-4-ones through oxidation of homopropargyl alcohols and subsequent isomerization, intramolecular addition of enol to allenic ketone has been developed. This methodology provides an efficient and promising approach to the structurally and pharmaceutically interesting pyrano[2,3-d]pyrimidine-2,5-dione nucleoside and benzopyran-4-one

  已经开发了通过高炔丙醇的氧化和随后的异构化，将烯醇分子内加成到烯丙基酮中的新颖，快速，有效的双环嘧啶核苷和苯并吡喃-4-酮的合成方法。这种方法为结构和药学上有趣的吡喃并[2,3 - d ]嘧啶-2,5-二酮核苷和苯并吡喃-4-酮衍生物提供了有效而有前途的方法。
• Study of Substituted Formylchromones
  作者：Hafez M. El-Shaaer、Pavol Zahradník、Margita Lácová、Mária Matulová

  DOI：10.1135/cccc19941673

  日期：——

  Substituted derivatives of 2- and 3-formylchromone were synthesized and studied by IR, ¹³C and ¹H NMR spectroscopy and the AM1 quantum chemical method. Energy and electron distribution calculations confirm the preference of the synplanar conformation in 3-formylchromones. The calculated charges on the carbon atoms correlate well with the experimental ¹³C chemical shifts. Substituents bonded to the aromatic nucleus have only small effect on the electron structure of the pyrone ring.

  对2-和3-甲酰基香豆素的衍生物进行了合成和研究，通过红外光谱、¹³C和¹H核磁共振光谱以及AM1量子化学方法进行了研究。能量和电子分布计算证实了3-甲酰基香豆素中synplanar构象的优先性。计算得到的碳原子的电荷与实验中的¹³C化学位移很好地相关。芳香核上的取代基对吡喃环的电子结构仅有轻微影响。
• Derivatives of acetoacetic acid. Part VIII. The synthesis of coumarins from aryl acetoacetates
  作者：R. N. Lacey

  DOI：10.1039/jr9540000854

  日期：——
• Wittig, Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 179
  作者：Wittig

  DOI：——

  日期：——