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Merck
CN

261432

香豆灵酸甲酯

98%

别名:

2-吡喃酮-5-甲酸甲酯, 2-氧-2H-吡喃-5-羧酸甲酯

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经验公式（希尔记法）:
C7H6O4
化学文摘社编号:
6018-41-3
分子量:
154.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24855810
EC Number:
227-871-1
Beilstein/REAXYS Number:
126301
MDL number:
MFCD00010120

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产品名称

香豆灵酸甲酯, 98%

InChI key

HHWWWZQYHPFCBY-UHFFFAOYSA-N

InChI

1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3

SMILES string

COC(=O)C1=COC(=O)C=C1

assay

98%

form

solid

bp

178-180 °C/60 mmHg (lit.)

mp

65-67 °C (lit.)

functional group

ester

Quality Level

200

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相关类别

Application

Methyl coumalate has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.

General description

Methyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000516446
0000516446
0000242937
0000091366
0000242937

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Aromatics from pyrones: para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate.
Kraus GA, et al.
Green Chemistry, 13(10), 2734-2736 (2011)
Diels-Alder reaction of methyl coumalate with 1, 3-dienes.
Imagawa T, et al.
Tetrahedron, 30(14), 2227-2231 (1974)
Quinolizinium Compounds by Cyclization of Pyridones from Methyl Coumalate and ?-Phenylethylamines.
Wiley RH, et al.
Journal of the American Chemical Society, 75(18), 4482-4484 (1953)
Suqing Zheng et al.
Organic letters, 11(17), 3978-3981 (2009-08-13)
A phosphine-catalyzed [4 + 3] annulation of modified allylic carbonates with methyl coumalate was developed. This strategy offered a powerful method for the construction of bicyclo[3.2.2]nonadiene skeleton with high stereoselectivity.

商品

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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