2-methyl-7,8-benzochromone | 54965-49-0

• 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: 2-methyl-7,8-benzochromone
• 英文别名: 2-methyl-4H-naphtho<1,2-b>pyran-4-one；2-methyl-naphtho<1,2-b>pyran-4-one；2-methyl-benzo[h]chromen-4-one；2-Methyl-benzo[h]chromen-4-on；2-methyl-4H-naphtho[2,1-b]pyran-4-one；2-Methyl-naphtho<1,2-b>-4-pyron；2-Methyl-4H-naphtho[1,2-b]pyran-4-one；2-methylbenzo[h]chromen-4-one
• CAS: 54965-49-0
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: HSULZQNMIJZSHG-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：

  2-methyl-7,8-benzochromone 在 三氯化铝 、 sodium ethanolate 作用下， 以 乙醇 、 xylene 为溶剂， 反应 45.0h， 生成 8-benzoyl-10-(3-nitrophenyl)-7-oxo-7a,8,9,10-tetrahydronaphtho[1,2-b]chromene-9-carboxylic acid
  参考文献：
  名称：

  Soliman, Ahmed Youssef; Mahmoud, Mahmoud Refai; Bakeer, Hadeer Mohamed, Acta Chimica Hungarica, 1991, vol. 128, # 3, p. 345 - 354

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(1-hydroxynaphthalen-2-yl)butane-1,3-dione 在 三乙基硅烷 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以76 %的产率得到2-methyl-7,8-benzochromone
  参考文献：
  名称：

  使用 AgOTf/[Si]H 系统通过切换氢硅烷从二酮发散合成色酮和色满酮

  摘要：

  开发了一种使用AgOTf/[Si]H通过切换氢硅烷的还原偶联环化从共同底物高效且发散地合成色酮和色满酮的方法。机理研究结果表明，在PhMeSiH条件下，反应最初发生环化形成色酮，随后可被还原生成色酮。当氢硅烷换成EtSiH时，反应路线在色酮处停止，CC不能进一步还原。这种新颖、温和的方案具有广泛的官能团兼容性、高产品多样性以及在构建生物相关色酮或色满酮衍生物方面的实用性。

  DOI：

  10.1016/j.tet.2024.134087

文献信息

• 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。
• DNA-PK INHIBITORS
  申请人：Martin Morrison Barr Niall

  公开号：US20070238729A1

  公开（公告）日：2007-10-11

  The invention relates to the use of compounds of formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, in the preparation of a medicament for inhibiting the activity of DNA-PK, wherein R 1 and R 2 are independently hydrogen, an optionally substituted C 1-7 alkyl group, C 3-20 heterocyclyl group, or C 5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; X and Y are selected from CR 4 and O, O and CR′ 4 and NR″ 4 and N, where the unsaturation is in the appropriate place in the ring, and where one of R 3 and R 4 or R′ 4 is an optionally substituted C 3-20 heteroaryl or C 5-20 aryl group, and the other of R 3 and R 4 or R′ 4 is H, or R 3 and R 4 or R″ 4 together are -A-B—, which collectively represent a fused optionally substituted aromatic ring. The compounds also selectively inhibit the activity of DNA-PK compared to PI 3-kinase and/or ATM.

  本发明涉及使用式(I)的化合物及其异构体、盐、溶剂合物、化学保护形式和前药，在制备抑制DNA-PK活性的药物方面有用。其中，R1和R2独立地表示氢、可选取代的C1-7烷基、C3-20杂环基或C5-20芳基，或者与它们连接的氮原子一起形成可选取代的含有4到8个环原子的杂环环；X和Y选自CR4和O，O和CR'4以及NR"4和N，其中不饱和度在环中适当位置，其中R3和R4或R'4中的一个为可选取代的C3-20杂芳基或C5-20芳基，而另一个为H，或者R3和R4或R"4在一起为-A-B-，代表一种融合的可选取代芳香环。这些化合物与PI 3-激酶和/或ATM相比，具有选择性地抑制DNA-PK的活性。
• Cheema et al., Journal of the Chemical Society, 1932, p. 925,930
  作者：Cheema et al.

  DOI：——

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

  DOI：——

  日期：——
• Infrared spectra and theoretical study of methyl, formyl and acetyl derivatives of chromones
  作者：Hafen Mohamad El-Metwally El-Shaaer、Alexander Perjéssy、Pavol Zahradník、Margita Lácová、Zora Šusteková

  DOI：10.1007/bf00819522

  日期：1993.5

  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.