69948-55-6

Basic information

• Product Name: 2-Cyclohexen-1-one, 3-(2,2-dimethylhydrazino)-
• CAS NO: 69948-55-6
• Molecular Formula: C8H14N2O
• Molecular Weight: 154.212
• Mol File: 69948-55-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 3-(2,2-dimethylhydrazino)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 3-(2,2-dimethylhydrazino)-(69948-55-6)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 3-(2,2-dimethylhydrazino)-(69948-55-6)

Safety Data

• Hazardous Substances Data: 69948-55-6(Hazardous Substances Data)

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 57-14-7 N,N-Dimethylhydrazine 
• 30182-67-3 1,3-Cyclohexanedione 

Downstream Products

• 124015-87-8 2-methyl-1,3-cyclohexanedione-dimethylhydrazone 
• 311813-45-3 2-amino-4-(4-bromophenyl)-1-(dimethylamino)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 562-13-0 2,2-dimethyl-1,3-cyclohexanedione 
• 25112-82-7 2-ethyl-2-methyl-cyclohexane-1,3-dione 
• 22381-56-2 2-benzylcyclohexane-1,3-dione 
• 18456-78-5 2-ethylcyclohexane-1,3-dione 
• 32561-55-0 2-methyl-2-(prop-2-yn-1-yl)cyclohexane-1,3-dione 
• 16868-65-8 2-(prop-2-yn-1-yl)cyclohexane-1,3-dione 
• 127311-61-9 2-benzyl-2-methyl-cyclohexane-1,3-dione 
• 1514930-68-7 2,4-diamino-10-(dimethylamino)-6-oxo-5-phenyl-5,6,7,8,9,10-hexahydrobenzo[b][1,8]-naphthyridine-3-carbonitrile 
• 113565-96-1 4-phenyl-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 

Relevant articles and documents

Synthesis of α,β-Dicarbonylhydrazones by Aerobic Manganese-Catalysed Oxidation

A practical, simple, and efficient manganese-catalysed oxidation of C(sp2)?H bond in readily available β-carbonylenehydrazine under aerobic conditions has been developed. This protocol exhibits a wide range of functional group tolerance in β-carbonylenehydrazines to afford α,β-dicarbonylhydrazones. Experimental and theoretical results suggest that the reaction very likely proceeds through a radical pathway via a hydrogen-atom-transfer process promoted by a MnIII species. (Figure presented.).

Regioselective alkylations of cyclic 1,3-diketones via metalated dimethylhydrazones

Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N- alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation.The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono- and polyalkylated 1,3- diketones 7 in good yields.

ASYMMETRIC MICHAEL ADDITION/LACTAMIZATION VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDRO-2,5(1H,3H)-QUINOLINEDIONES

An efficient and highly diastereo- and enantioselective annulation of cyclic 1.3-diketones to tetrahydro-quinolinediones of type 4 and 5 in good overall yields is described.The key step is the Michael addition of the corresponding lithiated SAMP-/RAMP-hydrazones to arylidenemalonates followed by lactamization with virtually complete asymmetric induction (de,ee98percent).