19352-94-4

Usage

InChI:InChI=1/C8H13NO/c1-8(10)4-7-9-5-2-3-6-9/h4,7H,2-3,5-6H2,1H3

Upstream product

• 123-75-1 pyrrolidine 
• 87419-51-0 3-Oxo-2,3-dihydrothiophene 1,1-dioxide 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 51731-17-0 trans-4-methoxy-3-buten-2-one 
• 23074-57-9 4-ethoxybut-3-en-2-one 
• 14716-77-9 1-(1-imidazolyl)-1-buten-3-one 
• 91860-01-4 1-(3-oxo-1-buten-1-yl)-3-methylimidazolium iodide 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 

Downstream Products

• 1367352-54-2 C₁₆H₂₆N₂O 
• 87005-15-0 α-bromoacetoacetaldehyde 
• 223761-49-7 4-(Pyrrolidin-1-yl)but-3-in-2-on 

Relevant academic research and scientific papers

A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism

An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studie

Scalable synthesis of highly reactive 1,3-diamino dienes from vinamidinium salts and their use in Diels-Alder reactions

A practical and chromatography-free synthesis of vinamidinium salts and their use as diene precursors in Diels-Alder reactions is reported. Additionally, 1,3-dipyrrolidino-1,3-butadiene was shown to be significantly more reactive than Rawal's diene in a c

1-amino-3-siloxy-1,3-butadienes: Highly reactive dienes for the Diels- Alder reaction

1-Amino-3-siloxy-1,3-butadienes represent a novel class of heteroatom- containing dienes with several useful properties. These dienes can be prepared efficiently by deprotonation of readily available vinylogous amides with potassium hexamethylsilazide, followed by silylation of the corresponding potassium enolates. This protocol has been found to be quite general for the preparation of various dienes containing different silyl and amino groups. Amino siloxy dienes readily undergo [4 + 2] cycloadditions with a wide range of electron-deficient dienophiles. The reactions generally occur under very mild conditions to afford the corresponding [4 + 2] adducts in high yields and with complete regioselectivity. High endo selectivity is observed in the case of N-phenylmaleimide and methacrolein. Other cycloadducts are usually obtained as mixtures of endo/exo diastereomers. The cycloadducts are versatile synthetic intermediates. They can be subjected to deprotonation, reduction, and Wittig olefination without any hydrolysis or elimination. In addition, the elimination of the amino group can be cleanly accomplished under acidic conditions leading to the formation of enones. A variety of substituted cyclohexenones can be prepared by this procedure.

Synthesis of stacked 'push-pull' acetylenes

In view of possible solid-state polymerizations of crystalline stacked 'push-pull'-acetylenes 1, a series of compounds 1 has been synthesized (Scheme 3), and the results of X-ray analyses of 'push-pull'-acetylenes 1d,e,f are discussed. Of these three compounds, methyl 2-morpholinoacetylene carboxylate (1d) is by far the best candidate giving crystals with nicely stacked molecules (Fig. 3), Even in this case, however, stacking parameters d = 4,12 A and a = 31,6°are too large for allowing solid-state polymerizations.

Additions of nucleophiles to 3-oxo-2,3-dihydrothiophene 1,1-dioxides. Formation of vinyl sulfides, thioacetals and enaminones

3-Oxo-2,3-dihydrothiophene 1,1-dioxide (la) was prepared by oxidation of the commercially available 3methoxythiophene with dimethyldioxirane. Some other substituted 3-methoxythiophene derivatives were oxidized as well. Although the yields of these reactio

Michael additions to 3(2H)-thiophenone 1,1-dioxide

The addition of thiols and amines to 3(2H)thiophenone 1,1-dioxide takes place with extrusion of sulfur dioxide, furnishing in high yields the corresponding vinyl sulfides and enamines. Addition of dithiols afforded the corresponding thioacetals. The rates of the Michael addition and the extrusion reaction are strongly influenced by the solvent employed. In ethanol, sulfur dioxide extrusion took place even at room temperature.

Reactivities of 3-(1-Azolyl)-2-alken-1-ones and the Related Compounds With Pyrrolidine

From the rate constants of the reaction with pyrrolidine, the reactivities of 3-(1-azolyl)-2-alken-1-ones with nucleophiles were evaluated to be rather high.Especially the reactivities of the quarternary salts of 3-(1-imidazolyl)-2-alken-1-ones were nearly equal to those of 3-chloro-2-alken-1-ones.In conclusion, 3-(1-imidazolyl)-2-alken-1-ones satisfied the practical requirements for the starting materials of the synthesis of 3-hetero-substituted 2-alken-1-ones.

SYNTHESIS OF DERIVATIVES OF 3-OXOBUTANAL CONTAINING FUNCTIONAL GROUPS IN THE MESOMETHYLENE UNIT

The synthesis of 2-bromo-3-oxobutanal was realized by the bromination of 1-dialkylamino-1-buten-3-ones.The trans-enol form predominates in solutions.The direct nitration of 1,1-diethoxy-3-butanol leads to 2-nitro-3-oxobutanal.