5394-63-8 Usage
Description
It is usually used as intermediate or raw material in the chemistry synthesis. For example, 2,2,6-Trimethyl-4H-1,3-dioxin-4-one can act as the starting material to produce N-alkenyl acetoacetamides through reaction with imines.1 This substance can also be involved in the preparation of acetoacetamide derivatives, which result in the formation of the pyrrole amides via oxime of the acetoacetamides.2 Moreover, this chemical may be introduced to promote the acetoacetylation of O-(hydroxypropyl)cellulose for generating O-(acetoxypropyl)cellulose.3 In addition, this chemical may be used to yield β-keto esters and β-ketoamides through the reaction with secondary or tertiary alcohols (including chiral ones) or primary or secondary amines.4
Reference
Dannibale, A.; Pesce, A.; Resta, S.; Trogolo, C., Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides. Tetrahedron Lett. 1996, 37, 7429-7432.
Huggins, M.; Barber, P.; Florian, D.; Howton, W., Short, Efficient Syntheses of Pyrrole -Amides. Synth. Commun. 2008, 38, 4226-4239.
Pawlowski, W. P.; Gilbert, R. D.; Fornes, R. E.; Purrington, S. T., ACETOACETYLATION OF O-(HYDROXYPROPYL)CELLULOSE BY 2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE. Carbohydr. Res. 1986, 156, 232-235.
Sridharan, V.; Ruiz, M.; Menendez, J. C., Mild and High-Yielding Synthesis of beta-Keto Esters and beta-Ketoamides. Synthesis 2010, 1053-1057.
Chemical Properties
Dark brown liquid
Uses
Different sources of media describe the Uses of 5394-63-8 differently. You can refer to the following data:
1. Diketene-Acetone Adduct can be used in place of diketene in many reactions. As a transportable form of diketene, it is especially important in those countries, where the transportation of diketene is not allowed or at least not desired.
2. 2,2,6-Trimethyl-1,3-dioxin-4-one is used in the synthesis of dihydropyrimininones as picomolar sodium iodide symporter inhibitors. It is also used in the synthesis of resorcinol amide Hsp90 Inhibitor AT13387. It is used in the synthesis of acetylketene by flash pyrolysis.
Application
2,2,6-Trimethyl-4H-1,3-dioxin-4-one generates unstable acetylketene together with acetone when heated above 120 ℃. Subsequent condensation with isocyanates, arylcyanates, or substituted cyanamides gives access to a wide range of 1,3-oxazine derivatives. Furthermore, diketene – acetone adduct can also be used for the preparation of a variety of compounds that are not accessible from diketene.
Chemical Reactivity
Diketene – acetone adduct (2,2,6-Trimethyl-4H-1,3-dioxin-4-one) can be regarded as a stabilized form of diketene. It can be safely transported and may conveniently be used instead of diketene in many reactions. For example, it reacts with alcohols and amines to yield acetoacetates and acetoacetamides, respectively. Diketene – acetone adduct generates unstable acetylketene together with acetone when heated above 120 ?C. Subsequent condensation with isocyanates, arylcyanates, or substituted cyanamides gives access to a wide range of 1,3-oxazine derivatives. Furthermore, diketene – acetone adduct can also be used for the preparation of a variety of compounds that are not accessible from diketene.
Check Digit Verification of cas no
The CAS Registry Mumber 5394-63-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,9 and 4 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 5394-63:
(6*5)+(5*3)+(4*9)+(3*4)+(2*6)+(1*3)=108
108 % 10 = 8
So 5394-63-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3
5394-63-8Relevant articles and documents
A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type
Bodenschatz, Kevin,St?ckl, Julia,Winterer, Markus,Schobert, Rainer
, (2021/05/31)
A flexible synthetic route to the 16-membered tetramate-embedding macrocyclic scaffold present in various polycyclic tetramate macrolactams (PTMs) was developed which differs from the seminal synthesis of ikarugamycin by Boeckman Jr. in protecting groups and the order of connections. We also devised a short approach to various stereoisomers of the 5/5/6-tricarbocyclic motif found in discodermide and other PTMs, starting from the Weiss’ diketone.
Rapid and structurally diverse synthesis of multi-substituted β-keto amide derivatives based on a dioxinone scaffold
Fuse, Shinichiro,Yoshida, Hayato,Oosumi, Kazuya,Takahashi, Takashi
supporting information, p. 4854 - 4860 (2014/08/05)
A sequential diversification approach for the synthesis of various multi-substituted β-keto amide derivatives based on a simple and readily available dioxinone scaffold was developed. The process involves: (1) nucleophilic addition of the scaffold to an aldehyde, and a subsequent one-pot dehydration; (2) palladium-catalysed cross-coupling of the scaffold with either an arylboronic acid pinacol ester, or CO and an aliphatic amine; and (3) nucleophilic addition of either an aliphatic amine or an arylamine, or a hetero-Diels-Alder reaction of isocyanate/isothiocyanate, with an acylketene generated in situ from the dioxinone scaffold. Multi-substituted β-keto amides were synthesized in a sequential four-component coupling process based on a dioxinone scaffold.
Sodium carbonate as a solid-phase reagent for the generation of acetylketene
Bell, Kelcey,Sadasivam, Dhandapani V.,Gudipati, Indra Reddy,Ji, Hua,Birney, David
body text, p. 1295 - 1297 (2009/09/06)
Reaction of a toluene solution of 3-oxobutanoyl chloride (14) with Na2CO3 in the presence of a catalytic amount of triethylamine at -78 °C generates a solution of acetylketene (2), the dimer of which was isolated. Acetylketene (2) was trapped with 2-propanone, 2-propanol, and ethyl vinyl ether.
