59557-05-0

Usage

Chemical Properties

Clear, colorless or pale yellow liquid; minty aroma.

InChI:InChI=1/C14H24O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-10,12-13H,5-8H2,1-4H3/t10-,12+,13-/m0/s1

Upstream product

• 3623-52-7 isomenthol 
• 141-97-9 ethyl acetoacetate 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 
• 2216-51-5 (-)-menthol 
• 674-82-8 4-methyleneoxetan-2-one 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 105-45-3 acetoacetic acid methyl ester 
• 42490-66-4 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 2033-24-1 cycl-isopropylidene malonate 
• 75-36-5 acetyl chloride 
• 1694-31-1 tert-butyl acetoacetate 
• 591-60-6 butyl acetoacetate 

Downstream Products

• 116395-59-6 3-amino-crotonic acid menthyl ester 
• 85720-00-9 l-menthyl 7-methyl-3-oxo-6-octenoate 
• 74965-53-0 3-Oxo-oct-7-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 159253-86-8 (Z)-(-)-(1R,2S,5R)-menthyl 3-oxo-2-phenylmethylene butanoate 
• 121004-10-2 (S)-2-Acetyl-3-methyl-nonanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 158818-65-6 (1R,2S)-2-Methyl-4,6-dioxo-cyclohexanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 200569-84-2 (E)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylsulfanyl)-3-hydroxy-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 158393-61-4 2-Diazo-4-methyl-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 158393-62-5 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl-2-diazo-3-phenylpropanoate 
• 158393-63-6 2-Diazo-succinic acid 4-tert-butyl ester 1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 259250-89-0 (-)-Menthyl 4-(1-hydroxycyclohexyl)-3-oxobutanoate 
• 591-60-6 butyl acetoacetate 
• 540798-46-7 (-)-menthyl 2-fluoro-3-oxobutanoate 

Relevant academic research and scientific papers

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one-step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.

Addition of Diazo Compounds ipso -C-H Bond to Carbon Disulfide: Synthesis of 1,2,3-Thiadiazoles under Mild Conditions

We describe here an operationally simple and straightforward synthesis method for a series of diverse 4,5-disubstituted 1,2,3-thiadiazoles via the nucleophilic addition of α-diazo carbonyl compounds to carbon disulfide. This method features using abundant and inexpensive carbon disulfide under mild reaction conditions.

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usi

Direct Carboxylation of the Diazo Group ipso-C(sp2)-H bond with Carbon Dioxide: Access to Unsymmetrical Diazomalonates and Derivatives

The direct carboxylation of the ipso-C(sp2)-H bond of a diazo compound with carbon dioxide under mild reaction conditions is described. This method is transition-metal-free, uses a weak base, and proceeds at ambient temperature under atmospheric pressure in carbon dioxide. The carboxylation exhibits high reactivity and is amenable to subsequent diversification. A series of unsymmetrical 1,3-diester/keto/amide diazo compounds are obtained with moderate to excellent yields (up to 99%) with good functional group compatibility.

(3R)-L-MENTHYL 3-HYDROXYBUTYRATE, PROCESS FOR PRODUCING THE SAME, AND SENSATE COMPOSITION COMPRISING THE SAME

The present invention provides a cooling component or sensate component which has further strong cooling intensity and is excellent in the persistency or refresh-feeling and cool-feeling, a sensate composition comprising the same, and various products comprising the sensate composition. The present invention relates to, as a cooling component or sensate component, (3R)-1-menthyl 3-hydroxybutyrate represented by the following formula (I):

Mild and high-yielding synthesis of β-keto esters and β-ketoamides

In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and-keto esters and-ketoamides were normally obtained in quantitative yields.

Diversity-oriented synthesis of quinolines via Friedlaender annulation reaction under mild catalytic conditions

An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlaender annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using eerie ammonium, nitrate as a catalyst (10 mol %) at ambient temperature in 45 min, A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R1 and R 2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results.

PROCESS FOR PRODUCING (3S)-I-MENTHYL 3-HYDROXYBUTYRATE AND SENSATE COMPOSITION

The present invention provides a cooling component or sensate component which does not have undesirable stimulus feeling, bitterness and the like and is excellent in the persistence of refresh-feeling and cool-feeling, a sensate composition which comprise

Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate

An efficient and environmentally benign boric acid catalyzed protocol for the transesterification of ethyl acetoacetate with a variety of primary and secondary alcohols in good to excellent yields is described. The versatility of this transformation is demonstrated with problematic substrates such as propargyl alcohol and allyl alcohol, which are known to undergo Carroll rearrangement during transesterification.

USE OF SPECIFIC MENTHYL 3-OXOCARBOXYLIC ACID ESTERS AS PHYSIOLOGICALLY ACTIVE COOLING SUBSTANCES

The use is described of a compound of the formula (I) or (ent-I) or a blend consisting of two, three or more compounds of the formula (I) or (ent-I) (a) as a cooling substance for non-therapeutic purposes or (b) for the production of a medicament, wherein in each of the formulae (I) and (ent-I) R1, R2, R3, R4 and R5 mutually independently in each case mean hydrogen or a linear, branched or cyclic, saturated or unsaturated hydrocarbon residue having 1 to 4 carbon atoms.