5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical Properties

Melting point:

83-84 °C

Boiling point:

385.9±42.0 °C(Predicted)

Density 

1.303

storage temp. 

2-8°C

pka

4.50±1.00(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C8H10O5/c1-4(9)5-6(10)12-8(2,3)13-7(5)11/h9H,1-3H3

InChIKey

WIIDJHLROTYVRD-UHFFFAOYSA-N

SMILES

O1C(=O)/C(=C(\O)/C)/C(=O)OC1(C)C

Safety Information

HS Code 

2932990090

5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione Usage And Synthesis

Description

5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Acetyl Meldrum's acid) is a pharmaceutical intermediate compound used in the preparation of Vinaxanthone. Vinaxanthone is a selective inhibitor of signal transduction factor 3A, phospholipase C (PLC), and FabI, and exhibits antibacterial activity.

Uses

Acetyl Meldrum''s Acid is used in preparation of Bicyclic β-Lactams/Oxazinones via Cycloaddition and metathesis starting from Acyl/Carbamoyl-dimethyl-dioxa-diones.

Synthesis

The general procedure for the synthesis of 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxo-4,6-dione from cyclic (sub)isopropyl malonate and acetyl chloride is as follows: GENERAL METHOD: Method A (adapted from Srensen et al:) 1. To a dichloromethane solution of Meldrum acid (1 eq.) was added dropwise pyridine (2 eq.) at 0 °C and stirred for 15 min. 2. to the reaction mixture was added the corresponding acyl chloride (1 eq.). 3. The reaction mixture was stirred at 0 °C for 1.5 hours, followed by continued stirring at room temperature for 1.5 hours. 4. Upon completion of the reaction, the reaction was quenched with 2M hydrochloric acid and extracted with dichloromethane. 5. The organic layers were combined, dried with sodium sulfate, filtered and concentrated in vacuum. 6. the residue is purified by silica gel chromatography using a hexane solution of 5% to 10% ethyl acetate (containing 1% acetic acid) as eluent to afford the target product 5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxo-4,6-dione (acyl Meldrum acid derivatives, nos. 11a-e, j, l, p).

References

[1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1003 - 1007
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1321 - 1340
[3] Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 403 - 410
[4] Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1427 - 1445
[5] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 10, p. 1303 - 1306

5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione(85920-63-4)Related Product Information

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