2,2-Dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-1,3-dioxane-4,6-dione 속성

2,2-Dimethyl-1,3-dioxane-4,6-dione MSDS

2,2-Dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-1,3-dioxane-4,6-dione C화학적 특성, 용도, 생산

개요

Meldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione, is an organic compound with the formula C6H8O4. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid. Yet Meldrum's acid has a high acidity with a pKa of 4.97, because like ascorbic acid, deprotonation at the methylene next to the carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.

화학적 성질

The compound appears as white to beige crystals. It has a melting point of 94-95℃ (decomposition), is insoluble in water, and is soluble in ethanol and acetone.

주요 응용

2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
    macrocyclic β-keto lactone
    4-pyridyl-substituted heterocycles
    2-substituted indoles
    isofraxidin.

용도

Meldrum's acid serves as an intermediate in a variety of organic synthesis reactions. It is commonly used as an alternative to acyclic malonic esters and generally acts as a C3O2 synthon in organic synthesis.

제조 방법

2,2-Dimethyl-1,3-dioxane-4,6-dione is usually prepared by condensation of malonic acid with acetone in acetic anhydride in the presence of sulfuric acid. Excellent yield of the product was achieved when acetic anhydride was added in a slow, controlled manner to a mixture of acetone, malonic acid and an acid catalyst.

일반 설명

2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pK_a 4.83) and steric rigidity. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.

Purification Methods

Crystallise the dione from Me2CO/H2O. It is a synthon for the C3 malonic acid moiety. [Arnette et al. J Am Chem Soc 106 6759 1984, Bihlmayer et al. Monatsh Chem 98 564 1967, Review: McNab Chem Soc, Rev 7 345 1978, Chan & Huang Synthesis 452 1982, Beilstein 19/5 V 8.]

2,2-Dimethyl-1,3-dioxane-4,6-dione 준비 용품 및 원자재

원자재

준비 용품

2,2-Dimethyl-1,3-dioxane-4,6-dione 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Xinxiang Hongqi District Houyuan Trading Co.,Ltd	+86-0373-3695376 +86-13937349994	HYJM@houyuanjm.com	China	300	58
Hebei Mojin Biotechnology Co., Ltd	+8613288715578	sales@hbmojin.com	China	12456	58
Shanghai UCHEM Inc.	+862156762820 +86-13564624040	sales@myuchem.com	China	6710	58
Henan Bao Enluo International TradeCo.，LTD	+86-17331933971 +86-17331933971	deasea125996@gmail.com	China	2503	58
Henan Fengda Chemical Co., Ltd	+86-371-86557731 +86-13613820652	info@fdachem.com	China	7845	58
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15928	58
Beijing Cooperate Pharmaceutical Co.,Ltd	010-60279497	sales01@cooperate-pharm.com	CHINA	1811	55
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
Shanghai Time Chemicals CO., Ltd.	+86-021-57951555 +8617317452075	jack.li@time-chemicals.com	China	1807	55

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