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7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛 | 7338-51-4

分子结构分类

有机化合物 - 有机杂环化合物 - 苯并吡喃

中文名称

7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛

中文别名

——

英文名称

7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-chromene-6-carbaldehyde

英文别名

6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one；7-hydroxy-5-methoxy-4-oxo-4H-chromene-6 carbaldehyde；7-hydroxy-5-methoxy-2-methyl-4-oxochromene-6-carbaldehyde

CAS

7338-51-4

化学式

C₁₂H₁₀O₅

mdl

——

分子量

234.208

InChiKey

HAYPHUYUTZEJQC-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

189 °C(Solv: water (7732-18-5))
沸点：

457.6±45.0 °C(Predicted)
密度：

1.384±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

1.5
重原子数：

17
可旋转键数：

2
环数：

2.0
sp3杂化的碳原子比例：

0.17
拓扑面积：

72.8
氢给体数：

1
氢受体数：

5

SDS

SDS：517683c6e42c19b08a0344e67cd944af

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
齿阿米素	visnagin	82-57-5	C₁₃H₁₀O₄	230.22

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	5,7-dimethoxy-2-methyl-4-oxo-4H-chromene-6-carbaldehyde	91903-64-9	C₁₃H₁₂O₅	248.235
甲基丁香色原酮	5-hydroxy-7-methoxy-2,6-dimethylchromone	480-12-6	C₁₂H₁₂O₄	220.225
——	5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one	5186-27-6	C₁₁H₈O₅	220.182
——	methyl 7-hydroxy-5-methoxy-2-methylchromone-6-carboxylate	138565-06-7	C₁₃H₁₂O₆	264.235
5,7-二羟基-2,6-二甲基-4H-苯并吡喃-4-酮	5,7-dihydroxy-2,6-dimethylchromone	491-48-5	C₁₁H₁₀O₄	206.198
——	6-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]-7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one	1373132-38-7	C₂₀H₁₆O₅	336.344
——	7-hydroxy-5-methoxy-2-methyl-6-<3-phenyl-3-oxoprop-1-en-1-yl>benzopyran-4(H)-one	108843-96-5	C₂₀H₁₆O₅	336.344
8-溴-7-羟基-5-甲氧基-2-甲基-4-氧代-4H-苯并吡喃-6-甲醛	8-bromo-6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one	100124-30-9	C₁₂H₉BrO₅	313.104
——	6-[(1E)-3-(4-bromophenyl)-3-oxoprop-1-en-1-yl]-7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one	1373132-40-1	C₂₀H₁₅BrO₅	415.24
——	6,7-dihydroxy-5-methoxy-2-methyl-4H-[1]benzopyran-4-one	16623-15-7	C₁₁H₁₀O₅	222.197
——	5-methoxy-8-methyl-2,6-dioxo-2H,6H-benzo<1,2:5,4-b'>dipyran	106038-24-8	C₁₄H₁₀O₅	258.23
——	3-Cyano-2,6-dioxo-5-methoxy-8-methyl-2H,6H-benzo<1,2-b:5,4-b'>dipyran	84734-97-4	C₁₅H₉NO₅	283.24
——	7-hydroxy-6-[3-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-3-oxoprop-1-enyl]-5-methoxy-2-methylchromen-4-one	188640-11-1	C₂₄H₂₀O₉	452.417
——	(E)-8-amino-6-(phenyl-3-oxoprop-1-enyl)-7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one	1373132-45-6	C₂₀H₁₇NO₅	351.359
5,6,7-三羟基-2-甲基-4H-苯并吡喃-4-酮	5,6,7-trihydroxy-2-methylchromone	5186-26-5	C₁₀H₈O₅	208.171
——	(E)-8-amino-6-(4-bromophenyl-3-oxoprop-1-enyl)-7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one	1373132-47-8	C₂₀H₁₆BrNO₅	430.255
——	(E)-8-amino-6-(3-methoxyphenyl-3-oxoprop-1-enyl)-7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one	1373132-46-7	C₂₁H₁₉NO₆	381.385
——	5-Methoxy-8-methyl-2,6-dioxo-pyrano[3,2-g]chromene-3-carbothioamide	112434-56-7	C₁₅H₁₁NO₅S	317.322
——	5-Methoxy-8-methyl-2,6-dioxo-pyrano[3,2-g]chromene-3-carbohydrazide	112434-54-5	C₁₅H₁₂N₂O₆	316.27
——	2-imino-5-methoxy-8-methyl-6-oxo-3-thiocarboxamide-2H,6H-benzo<1,2-b:5,4-b'>dipyran	112434-57-8	C₁₅H₁₂N₂O₄S	316.337
——	3-benzoyl-2-imino-5-methoxy-8-methyl-2H,6H-pyrano[3,2-g]chromen-6-one	112434-58-9	C₂₁H₁₅NO₅	361.354
——	3-carbohydrazide-2-imino-5-methoxy-8-methyl-6-oxo-2H,6H-benzo<1,2-b:5,4-b'>dipyran	112434-55-6	C₁₅H₁₃N₃O₅	315.285
——	7-hydroxy-5-methoxy-2-methyl-6-(4-phenyl-2-sulfanylidene-5,6-dihydro-1H-pyrimidin-6-yl)chromen-4-one	1373132-48-9	C₂₁H₁₈N₂O₄S	394.451
——	6-(benzimidazol-2-yl)-7-hydroxy-5-methoxy-2-methylchromone	212193-39-0	C₁₈H₁₄N₂O₄	322.32
——	2-[Amino-(5-methoxy-8-methyl-2,6-dioxo-pyrano[3,2-g]chromen-3-yl)methylene]propanedinitrile	112434-59-0	C₁₈H₁₁N₃O₅	349.302
——	6-[4-(4-bromophenyl)-2-sulfanylidene-5,6-dihydro-1H-pyrimidin-6-yl]-7-hydroxy-5-methoxy-2-methylchromen-4-one	1373132-50-3	C₂₁H₁₇BrN₂O₄S	473.347
——	2-[Amino-(2-imino-5-methoxy-8-methyl-6-oxo-pyrano[3,2-g]chromen-3-yl)methylene]propanedinitrile	112434-64-7	C₁₈H₁₂N₄O₄	348.318
——	8-bromo-7-hydroxy-5-methoxy-2-methyl-4-thioxo-4H-benzopyran-6-carbaldehyde	1239279-31-2	C₁₂H₉BrO₄S	329.171
——	7-hydroxy-5-methoxy-6-[4-(3-methoxyphenyl)-2-sulfanylidene-5,6-dihydro-1H-pyrimidin-6-yl]-2-methylchromen-4-one	1373132-49-0	C₂₂H₂₀N₂O₅S	424.477
——	3-(4-Fluorophenyl)-2-imino-5-methoxy-8-methylpyrano[3,2-g]chromen-6-one	1100363-95-8	C₂₀H₁₄FNO₄	351.334
——	3-(4-Chlorophenyl)-2-imino-5-methoxy-8-methylpyrano[3,2-g]chromen-6-one	1100363-96-9	C₂₀H₁₄ClNO₄	367.788
——	2-Imino-5-methoxy-8-methyl-3-(4-nitrophenyl)pyrano[3,2-g]chromen-6-one	1100363-97-0	C₂₀H₁₄N₂O₆	378.341
——	4-[2-(4-Aminophenyl)-2-oxo-ethyl]-2-imino-5-methoxy-8-methyl-6-oxo-3,4-dihydropyrano[3,2-g]chromene-3-carboxamide	174088-07-4	C₂₃H₂₁N₃O₆	435.436
——	3-(2,4-Dichlorophenyl)-2-imino-5-methoxy-8-methylpyrano[3,2-g]chromen-6-one	1100363-98-1	C₂₀H₁₃Cl₂NO₄	402.234
——	3-[amino-(3,5-diaminopyrazol-4-ylidene)methyl]-5-methoxy-8-methylpyrano[3,2-g]chromene-2,6-dione	112434-62-5	C₁₈H₁₅N₅O₅	381.348
——	4-[2-(4-Amino-phenyl)-2-oxo-ethyl]-2-imino-5-methoxy-8-methyl-6-oxo-3,4-dihydro-2H,6H-pyrano[3,2-g]chromene-3-carboxylic acid hydrazide	174088-08-5	C₂₃H₂₂N₄O₆	450.451
——	3-[amino-(3,5-diaminopyrazol-4-ylidene)methyl]-2-imino-5-methoxy-8-methylpyrano[3,2-g]chromen-6-one	112434-63-6	C₁₈H₁₆N₆O₄	380.363
——	5-methoxy-8-methyl-2,6-dioxo-N-[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]pyrano[3,2-g]chromene-3-carboxamide	1402580-85-1	C₂₄H₁₇N₃O₈S₂	539.546
——	2-imino-5-methoxy-8-methyl-6-oxo-N-[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]pyrano[3,2-g]chromene-3-carboxamide	1402580-84-0	C₂₄H₁₈N₄O₇S₂	538.562

反应信息

作为反应物：

描述：

7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛在二氧化锰、溶剂黄146 作用下，以甲醇、水、乙酸乙酯为溶剂，以80%的产率得到methyl 7-hydroxy-5-methoxy-2-methylchromone-6-carboxylate

参考文献：

名称：

Heterocyclic compounds: 2-styryl-4H-1-benzopyran-4-ones

摘要：

式(I)的化合物##STR1##其中：R.sub.1代表氢原子、较低的烷基基团、羟基或较低的烷氧基团，R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6、R.sub.7、R.sub.8和R.sub.11如描述中所定义。药物。

公开号：

US05409952A1
作为产物：

描述：

齿阿米素在 potassium dichromate 、硫酸作用下，以85%的产率得到7-羟基-5-甲氧基-2-甲基-4-氧代-4H-1-苯并吡喃-6-甲醛

参考文献：

名称：

磷叶立德化学。第 34 部分 Chromenone Phosphanylidene 和 Cyclobutylidene 衍生物的合成

摘要：

摘要亲核磷杂草烯叶立德与visnaginone 和khellinone 反应得到相应的亚膦基和呋喃色烯衍生物。此外，吡喃色烯是从色烯甲醛与磷枯草烯的反应中获得的。另一方面，亚膦基-亚环丁基及其二聚体是由呋喃色烯甲醛与相同的鏻试剂反应产生的。图形概要

DOI：

10.1080/10426507.2011.600741

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文献信息

Synthesis and reactions of some new benzopyranone derivatives with potential biological activities

作者：El-Sayed I. El-Desoky、Shar S. Al-Shihry

DOI：10.1002/jhet.5570450648

日期：2008.11

to yield the ylidene nicotinonitrile and pyridone derivatives 4,7,10a-b. Reaction of 3 with aniline or aniline acting on multiple function X-H (X = NH, O, S) at its ortho position afforded the corresponding anils, imidazolylfurochromene and azepines compounds 11-17. On the other hand, oxidation of visnagin afforded chromene-6-carboxaldehyde derivative 18 which was condensed with different aryl or (heteroaryl)

天然存在的化合物“ visnagine”衍生的visnaginone与烯丙基溴的反应生成了O-烯丙基visnaginone 1，对其进行了克莱森重排，生成了7-烯丙基苯并呋喃2衍生物。Vilsmeier Haack将2甲酰化可得到我们通用的起始化合物呋喃二烯-6-甲醛（3），将其与1,3-二酮环己烷，茚满二酮，丙二腈或氰基乙酸乙酯缩合，生成亚硝基烟腈和吡啶酮衍生物4,7,10a- b。3与苯胺或在其邻位作用于多功能XH（X = NH，O，S）的苯胺的反应位置得到相应的茴香，咪唑基呋喃酮和咪唑类化合物11-17。另一方面，通过氧化维斯那金，得到色烯-6-甲醛衍生物18，其与不同的芳基或（杂芳基）乙腈缩合，然后水解得到吡喃并[3,2 - g ]色烯-4,8-二酮衍生物20a- d和22。
Convenient synthesis of linear 2H,6H-pyrano[3,2-g] chromenes from natural occurring compound; visnagin

作者：Anhar Abdel-Aziem、Eslam R. El-Sawy、Gilbert Kirsch

DOI：10.1080/00397911.2019.1671455

日期：2019.12.17

Abstract A simple and convenient rout for the synthesis of linear 2-imino-2H,6H-pyrano[3,2-g] chromen-6-ones and 2H,6H-pyrano[3,2-g]chromene-2,6-diones has been described starting from natural occurring furochromone; visnagin (1). Ring opening of 1 yielded 6-formyl-7-hydroxy-5-methoxy-2-methylchromone (2), which underwent reaction with different acetonitrile derivatives furnished 2-imino-2H,6H-pyrano[3

摘要合成线性 2-imino-2H,6H-pyrano[3,2-g] chromen-6-ones 和 2H,6H-pyrano[3,2-g]chromene-2,6 的简便途径-二酮已被描述为从天然存在的呋喃色酮开始；维纳斯金 (1). 1 的开环产生 6-formyl-7-hydroxy-5-methoxy-2-methylchromone (2)，它与不同的乙腈衍生物反应得到 2-imino-2H,6H-pyrano[3,2-g] chromen- 6 个 (5a–h)。5a-h 的酸水解导致 2H,6H-吡喃并[3,2-g]色烯-2,6-二酮 (6a-h) 的形成。基于元素分析和光谱数据阐明了合成化合物的结构。美国国家癌症研究所 (NCI, Bethesda, USA) 选择了全部目标化合物，以单剂量 (10-5 M) 对 60 种人类癌细胞系进行体外抗癌活性。图形概要
Synthesis of Some Chromanone Derivatives and the Use of DNA in Evaluation of their Biological Activity

作者：El-Sayed I. El-Desoky、Emad. M. El-Telbani、Mahmoud A. Hammad

DOI：10.1515/znb-1998-0823

日期：1998.8.1

Abstract
6-Formyl-7-hydroxy-5-methoxy-2-pentamethylenechromanone (2) was prepared from the naturally occurring “Visnagin” and condensed with benzil, o-phenylenediamine and 3,4-diaminobenzophenone to give the corresponding imidazolylchromanone derivatives 3-5. Knoevenagel reaction of compound 2 with different active methylene compounds afforded benzodipyranone derivatives 12a - c which may be considered as analogues to the naturally occurring “Xanthyletin and Graveolone Compounds”. The structural formula of the new compounds were established by using different methods for their preparation in addition to the instrumental analyses. Some compounds in this study were biologically evaluated for their ability to bind to DNA.

摘要：从天然存在的“维斯纳金”制备了6-甲醛基-7-羟基-5-甲氧基-2-戊二亚甲基色酮(2)，并与苯二酮、邻苯二胺和3,4-二氨基苯基酮缩合，得到相应的咪唑基色酮衍生物3-5。化合物2与不同活性亚甲基化合物的Knoevenagel反应得到苯二吡喃酮衍生物12a-c，可视为天然存在的“黄酮类和格雷沃隆类化合物”的类似物。通过不同方法的制备和仪器分析，确定了新化合物的结构式。本研究中的一些化合物已经进行了生物学评估，以评估它们与DNA结合的能力。
Cyanoacetamide in heterocyclic chemistry: Synthesis, antitumor and antioxidant activities of some new benzothiophenes

作者：Serry A. A. El Bialy、Moustafa A. Gouda

DOI：10.1002/jhet.634

日期：2011.11

Cyanoacylation of 2‐amino‐tetrahydrobenzothiophene‐3‐carboxylate ethyl ester with 3‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐3‐oxopropanenitrile afforded cyanoacetamide 2. The later was utilized as key intermediate for the synthesis of 3‐substituted 2‐iminocoumarins 3, 4, 5, 6 and acrylamides 7a, b via Knoevenagel condensation with 2‐hydroxy‐1‐naphthaldehyde; 2‐hydroxybenzaldehyde; 1‐nitrosonaphthalen‐2‐ol; 7‐hydr

2-氨基-四氢苯并噻吩-3-羧酸乙酯与3-（3,5-二甲基-1H-吡唑-1-基）-3-氧代丙烷腈的氰化反应可得到氰基乙酰胺2。在后来被用作关键中间体的3-取代的2- iminocoumarins合成3，4，5，6和丙烯酰胺图7a，b 通过Knoevenagel缩合用2-羟基-1-萘醛; 2-羟基苯甲醛; 1-亚硝基萘-2-醇; 7-羟基-5-甲氧基-2-甲基-4-氧代-4 H-色烯-6-甲醛; 4-二甲氨基苯甲醛; 和4-哌啶-1-基苯甲醛的乙醇/哌啶溶液。导数7a，b用苯肼处理后不提供吡唑8a，b。此外，将2与4-氨基-1,5-二甲基-2-苯基-1 H-吡唑-3（2 H）-one和4,6-二甲基-1 H-吡咯并[2,3- b ]偶联吡啶-3-胺分别提供了derivatives衍生物9和10。将后来的衍生物10在乙酸中环化，得到吡啶并吡唑并三嗪11。最后，将2用二甲基甲酰胺-二甲基乙缩醛（
Synthesis and characterization of novel chromone Schiff base complexes as p53 activators

作者：Mohamad M.E. Shakdofa、Hanan A. Mousa、Ammar A. Labib、Amira S. Abd‐El‐All、Ahmed A. El‐Beih、Mohamed M. Abdalla

DOI：10.1002/aoc.4345

日期：2018.6

distorted octahedral geometry around the metal ions for all metal complexes except the nickel complex, which had a tetrahedral geometry. In addition, the ability of the newly prepared compounds to activate the tumour suppressor p53 in cancer cells was studied, with zinc and copper complexes showing promising activities for p53 ubiquitination compared with diphenylimidazole (reference drug).

制备了一系列色酮席夫碱配合物，并进行了分析和光谱表征。发现该配体充当经由安替比林部分的去质子化的羟基，偶氮甲碱氮原子和羰基氧原子共价或配位结合至金属离子的一元三齿配体。电子光谱和磁性测量均表明，除了具有四面体几何形状的镍络合物之外，所有金属络合物的金属离子周围的八面体或扭曲的八面体几何形状。此外，还研究了新制备的化合物激活癌细胞中肿瘤抑制因子p53的能力，与二苯基咪唑（参考药物）相比，锌和铜络合物显示出对p53泛素化有希望的活性。