6-acetyl-5-hydroxy-7-methoxy-2,2-dimethyl-4-chromanone | 124360-75-4

• 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-5-hydroxy-7-methoxy-2,2-dimethyl-4-chromanone
• 英文别名: 6-acetyl-5-hydroxy-7-methoxy-2,2-dimethyl-3H-chromen-4-one
• CAS: 124360-75-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: ZZNKKJQEANOWCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-acetyl-5-hydroxy-7-methoxy-2,2-dimethyl-4-chromanone 在 哌啶 、 吡啶 、 盐酸 、 thallium(III) nitrate trihydrate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 3-<2,4-Bis(benzyloxy)phenyl>-8,9-dihydro-5-methoxy-8,8-dimethyl-4H,10H-benzo<1,2-b:3,4-b'>dipyran-4,10-dione
  参考文献：
  名称：

  Synthesis of Parvisoflavones A and B.

  摘要：

  副黄酮 B (2'，4'，5-三羟基-2"，2"-二甲基吡喃并[5"，6"-g]异黄酮) (2) 是通过用硼氢化钠还原 7-[2，4-双(苄氧基)苯基]-2，3-二氢-5-甲氧基-2，2-二甲基-4H，6H-苯并[1，2-b ：用硼氢化钠和所得醇脱水后，再用三氯化硼进行脱烷基反应，就得到了 4-(苄氧基苯基)-2, 3-二氢-5-甲氧基-2, 2-二甲基-4H, 6H-苯并[1, 2-b : 5, 4-b']dipyrano-4, 6-二酮（7）。它的角异构体对维黄酮 A（2'，4'，5-三羟基-2"，2"-二甲基吡喃并[6"，5"-h]异黄酮）（1）也是由 3-[2，4-双（苄氧基）苯基]-8，9-二氢-5-甲氧基-8，8-二甲基-4H，10H-苯并[1，2，-b ：3，4-b']-二吡喃-4，10-二酮（15）的类似方法。

  DOI：

  10.1248/cpb.39.1704
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 氢氧化钾 、 三氯化铝 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 18.0h， 生成 6-acetyl-5-hydroxy-7-methoxy-2,2-dimethyl-4-chromanone
  参考文献：
  名称：

  从吡喃查耳酮合成吡喃异黄酮：Elongatin 及其角异构体的合成

  摘要：

  Elongatin（4',5-二羟基-2',5'-二甲氧基-2",2"-二甲基吡喃[5",6"-g]异黄酮）是通过相应吡喃查尔酮[6-(1 -oxo-3-phenyl-2-propenyl)-4-chromanone] 与硝酸铊 (III) 和 7-（4-苯甲酰氧基-2,5-二甲氧基苯基）-2,3-二氢-2,2 的区域选择性还原-二甲基-5-甲苯磺酰氧基-4H,6H-苯并[1,2-b:5,4-b']二吡喃-4,6-二酮与硼氢化钠-氯化钯，然后将所得醇脱水并水解。其角异构体（4',5-二羟基-2',5'-二甲氧基-2",2"-二甲基吡喃[6",5"-h]异黄酮）也以类似的方式由相应的吡喃查耳酮合成。

  DOI：

  10.1246/bcsj.62.826

文献信息

• Drug efficacy of novel 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans; evaluated via DNA gyrase inhibition, bacterial cell wall lesion and antibacterial prospective
  作者：Thangarasu Ponnusamy、Manikandan Alagumuthu、S. Thamaraiselvi

  DOI：10.1016/j.bmc.2018.05.016

  日期：2018.7

  In this study, novel 3-O-methoxy-4-halo, disubstituted-5,7-dimethoxy chromans with bacterial cell wall degrading potentials were synthesized, characterized and evaluated as DNA gyrase inhibitors and antibacterial agents. Compounds were showed a broad spectrum of antimicrobial activity against both Gram(+ve) bacteria (S. aureus (MTCC 3160), C. diphtheriae (MTCC 116), S. pyogenes (MTCC 442)) and Gram(-ve) bacteria (E. coli (MTCC 443), P. aeruginosa (MTCC 424), K. pneumoniae (MTCC 530)). Further, a molecular docking study was carried out to get more insight into the binding mode of present study compounds to target proteins (PDB ID: 2XCT (S. aureus DNA gyrase A), PDB ID: 3G75 (S. aureus DNA gyrase B), PDB ID: 3L7L (Teichoic acid polymerase). In the results, 14 > 20 > 24 > 12 > 18 > 17 were found as the most active against almost all executed activities in this study. The predicted Lipinski's filter scores, SAR, pharmacokinetic/pharmacodynamics, and ADMET properties of these compounds envisioned the druggability prospects and the necessity of further animal model evaluations of 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans to establish them as an effective and future antibiotics.
• Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone
  作者：Masao Tsukayama、Yasuhiko Kawamura、Hideo Tahara

  DOI：10.3987/com-91-5918

  日期：——

  Alpinumisoflavone (4', 5-dihydroxy-2".2"-dimethylpyrano[5", 6"-g]isoflavone) (1a) was synthesized by regioselective reduction of 7-(4-hydroxyphenyl)-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b:5, 4-b'] dipyran-4, 6-dione (15a) with NaBH4 and dehydration of the resultant alcohol, followed by demethylation with BC13. Its angular isomer (4', 5-dihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (2a) was synthesized from 3-(4-hydroxyphenyl)-8, 9-dihydro-5-tosyloxy-8, 8-dimethyl-4H,10H-benzo [1, 2-b:3, 4-b']dipyran-4, 10-dione (27a) in a similar manner.
• TSUKAYAMA, MASAO;KAWAMURA, YASUHIKO;TAMAKI, HIROTO;KUBO, TOMOYA;HORIE, TO+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 826-832
  作者：TSUKAYAMA, MASAO、KAWAMURA, YASUHIKO、TAMAKI, HIROTO、KUBO, TOMOYA、HORIE, TO+

  DOI：——

  日期：——
• Synthesis of Pyranoisoflavones from Pyronochalcones: Synthesis of Elongatin and Its Angular Isomer
  作者：Masao Tsukayama、Yasuhiko Kawamura、Hiroto Tamaki、Tomoya Kubo、Tokunaru Horie

  DOI：10.1246/bcsj.62.826

  日期：1989.3

  6H-benzo[1,2-b:5,4-b′]dipyran-4,6-dione with sodium boronydride–palladium chloride, followed by dehydration of the resultant alcohol and hydrolysis. Its angular isomer (4′,5-dihydroxy-2′,5′-dimethoxy-2″,2″-dimethylpyrano[6″,5″-h]isoflavone) was also synthesized from the corresponding pyronochalcone in a similar manner.

  Elongatin（4',5-二羟基-2',5'-二甲氧基-2",2"-二甲基吡喃[5",6"-g]异黄酮）是通过相应吡喃查尔酮[6-(1 -oxo-3-phenyl-2-propenyl)-4-chromanone] 与硝酸铊 (III) 和 7-（4-苯甲酰氧基-2,5-二甲氧基苯基）-2,3-二氢-2,2 的区域选择性还原-二甲基-5-甲苯磺酰氧基-4H,6H-苯并[1,2-b:5,4-b']二吡喃-4,6-二酮与硼氢化钠-氯化钯，然后将所得醇脱水并水解。其角异构体（4',5-二羟基-2',5'-二甲氧基-2",2"-二甲基吡喃[6",5"-h]异黄酮）也以类似的方式由相应的吡喃查耳酮合成。
• Synthesis of Parvisoflavones A and B.
  作者：Masao TSUKAYAMA、Yasuhiko KAWAMURA、Hiroto TAMAKI、Tokunaru HORIE

  DOI：10.1248/cpb.39.1704

  日期：——

  Parvisoflavone B (2', 4', 5-trihydroxy-2", 2"-dimethylpyrano[5", 6"-g]isoflavone) (2) was synthesized by regioselective reduction of 7-[2, 4-bis(benzyloxy)phenyl]-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b : 5, 4-b']dipyrano-4, 6-dione (7) with sodium borohydride and dehydration of the resultant alcohol, followed by dealkylation with boron trichloride. Its angular isomer, parvisoflavone A (2', 4', 5-trihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (1) was also synthesized from 3-[2, 4-bis(benzyloxy)phenyl]-8, 9-dihydro-5-methoxy-8, 8-dimethyl-4H, 10H-benzo[1, 2, -b : 3, 4-b']-dipyran-4, 10-dione (15) in a similar manner.

  副黄酮 B (2'，4'，5-三羟基-2"，2"-二甲基吡喃并[5"，6"-g]异黄酮) (2) 是通过用硼氢化钠还原 7-[2，4-双(苄氧基)苯基]-2，3-二氢-5-甲氧基-2，2-二甲基-4H，6H-苯并[1，2-b ：用硼氢化钠和所得醇脱水后，再用三氯化硼进行脱烷基反应，就得到了 4-(苄氧基苯基)-2, 3-二氢-5-甲氧基-2, 2-二甲基-4H, 6H-苯并[1, 2-b : 5, 4-b']dipyrano-4, 6-二酮（7）。它的角异构体对维黄酮 A（2'，4'，5-三羟基-2"，2"-二甲基吡喃并[6"，5"-h]异黄酮）（1）也是由 3-[2，4-双（苄氧基）苯基]-8，9-二氢-5-甲氧基-8，8-二甲基-4H，10H-苯并[1，2，-b ：3，4-b']-二吡喃-4，10-二酮（15）的类似方法。