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261432

香豆灵酸甲酯

Name: 香豆灵酸甲酯
Brand: ALDRICH

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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关于此项目

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

Assay:

98%

Form:

solid

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属性

Quality Level

200

assay

98%

form

solid

bp

178-180 °C/60 mmHg (lit.)

mp

65-67 °C (lit.)

functional group

ester

SMILES string

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

InChI

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

InChI key

HHWWWZQYHPFCBY-UHFFFAOYSA-N

说明

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[3.2.1.0^2,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.

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.

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

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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.

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)

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)

Phosphine-catalyzed [4 + 3] annulation for the synthesis of highly functionalized bicyclo[3.2.2]nonadienes.

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.

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全球贸易项目编号

货号	GTIN
261432-10G	04061833545751