565-68-4

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-1-PENTYN-3-OL is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique structure allows it to be easily modified and incorporated into complex molecular structures, contributing to the development of new and innovative pharmaceutical products.
Used in Organic Synthesis:
In the field of organic synthesis, 4-METHYL-1-PENTYN-3-OL is utilized as a key component in the creation of a wide range of organic compounds. Its reactivity and stability make it an ideal candidate for use in various chemical reactions, enabling the production of diverse organic molecules with potential applications in various industries, such as agriculture, materials science, and specialty chemicals.

InChI:InChI=1/C6H10O/c1-4-6(7)5(2)3/h1,5-7H,2-3H3

Upstream product

• 624-67-9 Propargylic aldehyde 
• 920-39-8 isopropylmagnesium bromide 
• 4301-15-9 ethynyldimagnesium dibromide 
• 78-84-2 isobutyraldehyde 
• 1066-26-8 sodium acetylide 
• 74-86-2 acetylene 
• 10575-81-2 1-bromo-4-methyl-1,2-pentadiene 
• 75-04-7 ethylamine 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 4301-14-8 acetylenemagnesium bromide 
• 925-90-6 ethylmagnesium bromide 
• 61077-67-6 4-methyl-1-(trimethylsilyl)pent-1-yn-3-ol 
• 65032-27-1 ethynylmagnesium chloride 

Downstream Products

• 14056-65-6 carbamic acid-(1-isopropyl-prop-2-ynyl ester) 
• 13531-82-3 4-methylpent-1-yn-3-one 
• 13643-05-5 4-methyl-1,2-pentadiene 
• 6986-70-5 4-Methyl-3-hydroxy-pentanon-(2) 
• 56438-76-7 3-benzoyloxy-4-methyl-pent-1-yne 
• 135613-99-9 (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 79157-49-6 <(Ethinyl)(isopropyl)methyl>-p-toluolsulfonat 
• 220650-24-8 2-[2-(3-hydroxy-4-methyl-1-pentynyl)phenyl]-1,3-dioxolane 
• 261785-36-8 1-(o-acetoxyphenyl)pent-4-methyl-1-yn-3-ol 
• 73522-97-1 , 4-methylpent-1-yn-3-ol 

Relevant academic research and scientific papers

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.

Discovery of Second Generation RORγ Inhibitors Composed of an Azole Scaffold

Starting from a previously reported RORγ inhibitor (1), successive efforts to improve in vivo potency were continued. Introduction of metabolically beneficial motifs in conjunction with scaffold hopping was examined, resulting in discovery of the second generation RORγ inhibitor composed of a 4-(isoxazol-3-yl)butanoic acid scaffold (24). Compound 24 achieved a 10-fold improvement in in vivo potency in a mouse CD3 challenge model along with significant anti-inflammatory effects in a mouse dermatitis model.

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles

The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.

Total syntheses of the dipyrrolobenzoquinone (+)-terreusinone enabled by an evaluation of 4-methylpent-1-yn-3-ols in the Larock indole synthesis

The Larock indolization between 4-methylpent-1-yn-3-ols (alkynols) and ortho-bromo and ortho-iodoanilines has been studied. Although the unprotected alkynol was an unviable substrate for the annulation reaction, protected derivatives did proceed to the indole products. Interestingly, this reaction does not appear to occur by the widely accepted mechanism for the Larock indolization of internal alkynes, but by the initial formation of a cross-coupled arylalkyne followed by 5-endo-dig cyclization. Importantly, when a chiral alkynol is used, the stereochemical integrity is retained in the indole product. Although this methodology could not be successfully extended to a double Larock indolization approach to terreusinone, two separate total syntheses evolved from these studies: A bidirectional, double Sonogashira-hydroamination approach and a one-pot Larock indolization- Sonogashira coupling followed by hydroamination. This work has not only confirmed the gross structure and absolute configuration of the photoprotecting natural product terreusinone, but also uncovered several novel applications of known reaction conditions that should find broad applications in the field of heteroaromatic construction.

Silver-catalysed intramolecular hydroamination of alkynes with trichloroacetimidates

Silver(i) complexes catalyse the intramolecular addition of trichloroacetimidates to alkynes. In the absence of a ligand, the selectivity of the reaction is dependent upon the nature of the counter-anion and solvent. The introduction of non-chelating nitrogeneous ligands suppresses competitive Bronsted acid catalysis, improving the yield and selectivity of the reaction.

Reactivity pattern of bis(propargyloxy) disulfides: Tandem rearrangements and cyclizations

Thirty-five substituted bis(propargyloxy) disulfides were successfully prepared in good to excellent yields, and their reactivity was found to be strongly dependent on the substitution pattern of the reactant. Inter alia they undergo surprising tandem sigmatropic rearrangements and cycloadditions. Three heretofore unknown product types were isolated and fully characterized: 6,7-dithiabicyclo[3.1.1]heptan-2-one 6-oxide derivatives, two isomeric 1,2-dithiete 1,1-dioxides (α,β-unsaturated four-membered cyclic thiosulfonates) from bis(propargyloxy) disulfides with α- or γ-alkyl-substituted propargyl groups, and two isomeric 2-oxa-5,7-dithiabicyclo[2.2.1]heptane 5-oxides from bis(propargyloxy) disulfides with α-tert-butyl- or α,α-dialkyl-substituted propargyl groups. Georg Thieme Verlag Stuttgart - New York.

Enantioselective copper-catalysed propargylic substitution: Synthetic scope study and application in formal total syntheses of (+)-anisomycin and (-)-cytoxazone

A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone. Copyright

Enantioselective copper-catalyzed propargylic amination

(Chemical Equation Presented) A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R = Ar) into their amine counterparts in high yield and with good selectivity (up to 88% ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA = diisopropylethylamine).

N-Vinylpyridinium tetrafluoroborate salts as reagents for the stereoselective and regioselective synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes

We had previously demonstrated the utility of N-vinylpyridinium tetrafluoroborate salts as novel electrophilic coupling partners in Pd(0)-catalyzed Suzuki cross-coupling reactions with aryl and vinyl boronic acids. We now report that these crystalline, air-stable, and non-hygroscopic salts are also useful reagents for the synthesis of symmetrical (2E,4E)-1,6-dioxo-2,4-dienes (diene diones), which in turn are valuable starting materials for the synthesis of various five-membered heterocycles. The optimization of reaction conditions and the scope and limitations of the reductive dimerization are discussed.