CAS: 82-57-5; 4-Methoxy-7-Methyl-5H-Furo[3,2-G]Chromen-5-One

该化合物是一个化学化合物,主要来源于以传统药用闻名的Visnaga植物(Ammi 相对纳加),被归类为furanocumarin, 一种含有furan和coumarin结构的化合物, 维斯nagin展示了一系列生物活动,包括潜在的抗炎,抗沙默和血管效应,使其对药理学研究感兴趣.该化合物的特点是晶体形式,在有机溶剂中可溶性.其分子结构有助于其再活动以及与生物系统的互动.在安全方面,由于潜在的毒性和对适当的实验室协议的需要,应谨慎处理该化合物.

英文名称4-Methoxy-7-Methyl-5H-Furo[3,2-G]Chromen-5-One
中文名称齿阿米素
IUPAC名称4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
其它别名Visnagin(6CI); 4-Methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one; 5-Methoxy-2-methyl-6,7-furan°Chrome; 5-Methoxy-2-methylfuran°Chromone; Desmethoxykhellin; Visnagidin; Visnagine
CAS编号82-57-5
MFCD编号:MFCD00005008
EINECS号:201-430-3
FDA UNII编号:P64438MLBW
分子式:C13H10O4分子量:230.22
产品CID: 1816298
产品分类生物化工 → 中草药成分

相似结构搜索
InChIKey: NZVQLVGOZRELTG-UHFFFAOYSA-N
InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
计算化学: 氢键受体数4.0氢键供体数*可旋转键数1.0

物理性质

熔点139-142 °C
沸点378.2±42.0 °C at 760 mmHg
闪点182.5±27.9 °C
密度1.3±0.1 g/cm3
PSA:52.58
LogP:2.26
折射率1.613
蒸汽压0.0±0.9 mmHg at 25°C
溶解性Soluble In DMSO (Up To 25 mg/mL) Or In Ethanol (Up To 25 mg/mL).
外观形态米色细结晶粉末
储存条件2-8°C
产品应用该化合物是一种从A.中分离出来的聚氯酸酯合成酶衍生呋喃,具有多种生物活动,抑制黑麦草的发芽和生长(IC50S=502和214微克/米);VISNAGIN(100微克/毫升)具有细胞毒性,并诱发HT-144黑皮瘤细胞的吸附性中毒;它减少了BV-2微闪光细胞中TNF-Α,IL-1Β和IFN-Γ分泌液中LPS刺激的增加,因为其使用浓度为50和100微克M.4VISNANGIN(25毫克/千克),可以防止老鼠中多氧素引发的心肌炎.

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

122822-92-8 = 82-57-5
反应条件:1.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

122822-89-3 = 82-57-5
反应条件:1.1 Reagents: Oxygen Catalysts: Palladium Chloride,Cuprous Chloride Solvents: Dimethylformamide,Water2.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane3.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran3.2 Reagents: Hydrochloric Acid Solvents: Methanol4.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

122822-87-1 = 82-57-5
反应条件:1.1 Reagents: Boron Trifluoride Etherate,Triethylamine Solvents: Tetrahydrofuran2.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran3.1 Reagents: Oxygen Catalysts: Palladium Chloride,Cuprous Chloride Solvents: Dimethylformamide,Water4.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane5.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran5.2 Reagents: Hydrochloric Acid Solvents: Methanol6.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

13007-92-6 + 2786-02-9 = 82-57-5
反应条件:1.1 Solvents: Tetrahydrofuran1.2 Reagents: Tetrabutylammonium Bromide2.1 Reagents: Acetyl Chloride Solvents: Dichloromethane2.2 -3.1 Reagents: Boron Trifluoride Etherate,Triethylamine Solvents: Tetrahydrofuran4.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran5.1 Reagents: Oxygen Catalysts: Palladium Chloride,Cuprous Chloride Solvents: Dimethylformamide,Water6.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane7.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran7.2 Reagents: Hydrochloric Acid Solvents: Methanol8.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

122822-91-7 = 82-57-5
反应条件:1.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran1.2 Reagents: Hydrochloric Acid Solvents: Methanol2.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

122822-90-6 = 82-57-5
反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane2.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran2.2 Reagents: Hydrochloric Acid Solvents: Methanol3.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

122822-88-2 = 82-57-5
反应条件:1.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran2.1 Reagents: Oxygen Catalysts: Palladium Chloride,Cuprous Chloride Solvents: Dimethylformamide,Water3.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane4.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran4.2 Reagents: Hydrochloric Acid Solvents: Methanol5.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3]

10549-76-5 = 82-57-5
反应条件:1.1 Reagents: Acetyl Chloride Solvents: Dichloromethane1.2 -2.1 Reagents: Boron Trifluoride Etherate,Triethylamine Solvents: Tetrahydrofuran3.1 Reagents: Methyl Iodide,Sodium Hydride Solvents: Tetrahydrofuran4.1 Reagents: Oxygen Catalysts: Palladium Chloride,Cuprous Chloride Solvents: Dimethylformamide,Water5.1 Reagents: Boron Trifluoride Etherate Solvents: Dichloromethane6.1 Reagents: Ethyl Acetate,Sodium Hydride Solvents: Tetrahydrofuran6.2 Reagents: Hydrochloric Acid Solvents: Methanol7.1 Catalysts: Nickel Solvents: Ethanol
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
作者:Yamashita,A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(19) 页码:4481-3

📜4-Methoxy-7-Methyl-9-Methylsulfanylfuro[3,2-G]Chromen-5-One置于镍体系中,用乙醇作为反应溶剂,以60%的收率获得产物齿阿米素
参考文献:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
标题:Reactions Of Alkylthio-Substituted Chromium Carbene Complexes With Alkynes: Application To Synthesis Of Visnagan
摘要:
DOI:10.1021/jo00280A002

海关参考信息

2905110000-甲醇
2908199090-其他酚的卤化衍生物
2908999090-其他酚的硝化衍生物
2918290000-其他含酚基羧酸
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-4459420-A
优先权日:1982-05-17
标题 :Pyrogallol synthesis of anti-atherogenic furochromones
发明人：GAMMILL RONALD B
权利人:UPJOHN CO
摘要:The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.

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主要参考文献

1: Selim AAMA, Ibrahim MA. Natural benzofuran derivatives as promising scaffold for alleviating Alzheimer symptoms: acetylcholinesterase inhibition, structure activity relationship and in silico studies. Nat Prod Res. 2024 Nov
21:1-7. doi: 10.1080/14786419.2024.2431998. Epub ahead of print.
955:176964. doi: 10.1016/j.scitotenv.2024.176964. Epub 2024 Oct 16. 19(1):20. doi: 10.1186/s12263-024-00756-3.

合成参考文献

参考文献:10.1371/journal.pone.0021922
摘要:Hunt PR, Son TG, Wilson MA, Yu Q, Wood WH, Zhang Y, Becker KG, Greig NH, Mattson MP, Camandola S, Wolkow CA. Extension of Lifespan in C. elegans by Naphthoquinones That Act through Stress Hormesis Mechanisms. PLoS ONE. 2011 Jul 13;6(7):e21922. doi: 10.1371/journal.pone.0021922.