4868-21-7

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 1487, 1977 DOI: 10.1021/ja00447a035The Journal of Organic Chemistry, 31, p. 977, 1966 DOI: 10.1021/jo01341a520

InChI:InChI=1/C11H18O2/c1-3-4-5-6-7-11(13)9-8-10(2)12/h4-5H,3,6-9H2,1-2H3/b5-4-

Upstream product

• 4868-20-6 2-hex-3c-enyl-5-methyl-furan 
• 62358-97-8 4,7-dioxo-octanal 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 21676-03-9 (Z)-3-hexenyl iodide 
• 69567-06-2 (N-methylanilino)prop-2-enenitrile 
• 6407-36-9 N-isopropyliden-cyclohexyl amine 
• 7051-43-6 undec-8-yne-2,5-dione 
• 55834-24-7 Z-1-(2-methyl-1,3-dioxolan-2-yl)non-6-en-3-one 
• 130236-77-0 (Z)-Hept-4-enoic acid methoxy-methyl-amide 
• 130236-79-2 methylcyclopropenyllithium 
• 114065-96-2 4-[2-((Z)-Hex-3-enyl)-3,4,4-trimethyl-oxazolidin-2-yl]-butan-2-one 
• 136749-84-3 (7aRS)-5-oxo-7a-methyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 
• 51575-14-5 (Z)-hex-3-enyllithium 
• 158197-54-7 2,2:5,5-bis(ethylenedioxy)-cis-8-undecene 

Downstream Products

• 488-10-8 cis-jasmone 
• 6261-18-3 trans-jasmone 

Relevant academic research and scientific papers

Synthesis of 1,4-diketones by reaction of bicyclic lactams derived from 4-oxoalkanoic acids with organolithium compounds

Bicyclic lactams obtained from ethyl 4-oxoalkanoates and 2-aminoethanol add saturated and unsaturated aliphatic lithium compounds forming the corresponding 1,4-diketones in 41-61% yield after acidic hydrolysis.

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.

Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone

Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.

Synthesis of cis-Jasmone

cis-Jasmone 1, an important olfactive ingredient of jasmine flower oil, was synthesized by starting from methyl 3-formylpropionate 2 in a 24 percent overall yield in 7 steps.

Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds

Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.

A facile synthesis of 1,4-diketones

1,4-Diketones may conveniently be synthesized by the addition of 2-methylcyclopropenyllithium to N-methoxy-N-methylcarboxamides followed by hydrolysis of intermediate cyclopropyl ketone adducts on silica gel. The new method has been applied to the synthesis of cis-jasmone.

(Z)-7-NITRO-3-HEPTENE AS CENTRAL INTERMEDIATE FOR THE SYNTHESIS OF JASMONE, METHYL JASMONATE, AND γ-JASMONOLACTONE

(Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmonolactone (16), three jasmin constituents.Conjugate addition of the title compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxo-dec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ-jasmonolactone.

Hydroacylation of Simple Alkyl Vinyl Ketones Using Organotetracarbonylferrates

Alkyl vinyl ketones were hydroacylated by organotetracarbonylferrates to the corresponding 1,4-diketones in good yields in dipolar aprotic solvents such as dimethylacetamide.The addition of 18-Crown-6 made an increase of the yields.

A NEW READY ROUTE TO 1,4-KETOALDEHYDES AND 1,4-DIKETONES WITH APPLICATION TO THE SYNTHESIS OF Z-JASMONE AND DIHYDROJASMONE

A new three-step synthesis in good overall yield of 1,4-ketoaldehydes and 1,4-diketones is described.The method involves two sequential coupling reaction of reagents with S-phenyl carbonochloridothioate in the presence of nickel(II) or iron(III) complexes as catalysts.Application of this reaction to the synthesis of Z-jasmone and dihydrojasmone is also described.

Synthesis and Application of Imidazole Derivatives: Preparation of Various Diketones from 1,n-Bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-diones

Reaction of 1,n-bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-dione (8) with an excess of Grignard reagent was examined.In the cases of n = 4 and 5, precursors (14) for synthesis of various asymmtric 1,4- and 1,5-diketones (12: R1 R2), respectively, were obtained in good yields by treating 8 with an excess of methylmagnesium iodide in ether followed by trimethylsilylation.In the case of n >/= 8, the two carbonyl groups of 8 were both attacked by the Grignard reagent, and the products (11: R1=R2=CH3) were convertible to symmetrical diketones (12: R1=R2=CH3) in good yields.In cases of n = 6 and 7, the mode of the Grignard reaction was transitional between the two types.Keywords - 2-acyl-1H-imidazole; 1,n-bis(1-methyl-1H-imidazol-2-yl)-1,n-alkanedione; diketone synthesis; asymmetric diketone; symmetric diketone; Grignard reaction; dihydrojasmone; cis-jasmone; muscone; 2-(1-hydroxy-1-alkyl)-1-methyl-1H-imidazole