22508-64-1

Usage

Uses

Used in Fragrance Industry:
4-Methyl-4-penten-1-ol is used as a fragrance ingredient for its slightly fruity scent, contributing to the creation of various perfumes and personal care products. Its unique aroma profile allows it to enhance the overall scent experience in these products.
Used in Chemical Synthesis:
In the realm of chemical synthesis, 4-Methyl-4-penten-1-ol serves as a building block for the production of other organic compounds, highlighting its versatility and importance in organic chemistry.
Used as an Industrial Solvent:
4-Methyl-4-penten-1-ol is utilized as a solvent in various industrial processes due to its ability to dissolve a range of substances, making it a valuable component in the manufacturing of different products.
Used in Production Methods:
4-METHYL-4-PENTEN-1-OL can be produced through two primary methods: the hydration of 4-methyl-4-penten-1-ene and the hydrogenation of 4-methyl-4-pentenal, both of which are significant in the chemical industry for generating this versatile compound.

InChI:InChI=1/C6H12O/c1-6(2)4-3-5-7/h7H,1,3-5H2,2H3

Upstream product

• 116131-45-4 3-chloro-3-methyl-tetrahydro-pyran 
• 99839-57-3 3-bromo-3-methyl-tetrahydro-pyran 
• 75-21-8 oxirane 
• 5674-01-1 2-methylallylmagnesium chloride 
• 115-11-7 isobutene 
• 563-47-3 3-Chloro-2-methylpropene 
• 503-30-0 trimethylene oxide 
• 6386-71-6 isopropenyllithium 
• 557-93-7 2-bromoprop-1-ene 
• 52387-48-1 4-methyl-pentyl hydroperoxide 
• 59529-72-5 4-methyl-1-nitrosooxy-pentane 
• 33324-92-4 (2-methylallyl)magnesium bromide 
• 2258-59-5 4-methyl-4-pentenoic acid methyl ester 
• 3973-43-1 4-methylpent-4-enal 

Downstream Products

• 114524-28-6 2-Methyl-2-phenylselanylmethyl-tetrahydro-furan 
• 115022-76-9 C₁₃H₁₈Cl₂O₂Te 
• 103348-73-8 (2R,3R)-2-(4-Methoxy-phenyl)-3-methyl-tetrahydro-pyran 
• 1001-75-8 4-methyl-4-pentenoic acid 
• 194297-38-6 1-(4-methyl-4-pentenoxy)cyclohexyl hydroperoxide 
• 131721-90-9 benzyl 4-methyl-4-pentenyl ether 
• 691900-28-4 N-(tert-butoxycarbonyl)-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 
• 1003-17-4 2,2-dimethyltetrahydrofuran 
• 157367-96-9 4-methyl-N-(4-methylpent-4-en-1-yl)benzenesulfonamide 
• 691900-33-1 N-formyl-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 
• 691900-13-7 N-ethynyl-4-methyl-N-(4-methyl-pent-4-enyl)-benzenesulfonamide 
• 691900-36-4 N-(2,2-dichlorovinyl)-N-(4-methylpent-4-enyl)-4-methylbenzenesulfonamide 
• 852245-21-7 (S)-5-Benzyloxy-2-methyl-pentane-1,2-diol 
• 852245-26-2 (S)-4-(3-Benzyloxy-propyl)-2,2,4-trimethyl-[1,3]dioxolane 

Relevant academic research and scientific papers

Total synthesis of the terpenoid buddledone A: 11-membered ring-closing metathesis

The first total synthesis of buddledone A was accomplished in seven steps from methyl ethyl ketone (MEK). The key step in the sequence featured an 11-membered ring formation by ring-closing metathesis.

Acyloxyetherifications mediated by lead tetracarboxylates

Lead(IV) tetracarboxylates are capable of reacting with unsaturated alcohols to give the products of cyclic acyloxyetherification, usually as a mixture of tetrahydro-2H-pyranyl and tetrahydrofuranyl compounds.

A TOTAL SYNTHESIS OF (+/-)-ZOAPATANOL AND DEMETHYL-ORF13811

Total syntheses of the spasmogenic diterpenoid zoapatanol and a demethyl analogue of the potent antigestational agent ORF 13811 are reported.A Ni0-catalysed coupling of MeMgBr with a dihydrofuran, and a carbo- or hydro-magnesiation of an acetylene were used to construct the trisubstituted alkenes in the key intermediates with high stereoselectivity.

Regio- and Stereoselectivity of the Intramolecular C-H Insertion by Cyclopropylidenes Bearing a Remote Oxido Substituent

(ω-Oxidoalkyl)cyclopropylidenes generated from (2,2-dibromo-1-methylcyclopropyl)-CH2-X-(CH2)n-OH (X=CH2 or O, n=1, 2) by the reaction with methyllithium underwent a regioselective intramolecular insertion into the C-H bond at the δ position to the carbenic carbon.The activation effect of the oxido substituent on the reactivity of C-H bonds is discussed on the basis of (1) the ratio of the insertion products to the rearrangement product allenyl alcohol, and (2) the endo stereoselectivity of the present insertion reactions.

Insect pheromones and their analogs. XI. Synthesis of 2,6-dimethylhepta-1,6-dien-3-ol acetate - the sex attractant of Pseudococcus comstocki

A new synthesis of 2,6-dimethylhepta-1,6-dien-3-ol acetate (I) - the sex attractant of The Comstock mealybug - has been developed.

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Modular Chemoenzymatic Synthesis of Terpenes and their Analogues

Non-natural terpenoids offer potential as pharmaceuticals and agrochemicals. However, their chemical syntheses are often long, complex, and not easily amenable to large-scale production. Herein, we report a modular chemoenzymatic approach to synthesize terpene analogues from diphosphorylated precursors produced in quantitative yields. Through the addition of prenyl transferases, farnesyl diphosphates, (2E,6E)-FDP and (2Z,6Z)-FDP, were isolated in greater than 80 % yields. The synthesis of 14,15-dimethyl-FDP, 12-methyl-FDP, 12-hydroxy-FDP, homo-FDP, and 15-methyl-FDP was also achieved. These modified diphosphates were used with terpene synthases to produce the unnatural sesquiterpenoid semiochemicals (S)-14,15-dimethylgermacrene D and (S)-12-methylgermacrene D as well as dihydroartemisinic aldehyde. This approach is applicable to the synthesis of many non-natural terpenoids, offering a scalable route free from repeated chain extensions and capricious chemical phosphorylation reactions.

Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation

Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols.

Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications

The intramolecular [2+2] photocycloaddition of 3-alkenyl-2-cycloalkenones was performed in an enantioselective fashion (nine representative examples, 54–86 % yield, 76–96 % ee) upon irradiation at λ=366 nm in the presence of an AlBr3-activated oxazaborolidine as the Lewis acid. An extensive screening of proline-derived oxazaborolidines showed that the enantioface differentiation depends strongly on the nature of the aryl group at the 3-position of the heterocycle. DFT calculations of the Lewis acid–substrate complex indicate that attractive dispersion forces may be responsible for a change of the binding mode. The catalytic [2+2] photocycloaddition was shown to proceed on the triplet hypersurface with a quantum yield of 0.05. The positive effect of Lewis acids on the outcome of a given intramolecular [2+2] photocycloaddition was illustrated by optimizing the key step in a concise total synthesis of the sesquiterpene (±)-italicene.

Diaminodiphosphine tetradentate ligand and ruthenium complex thereof, and preparation methods and applications of ligand and complex

The invention discloses a diaminodiphosphine tetradentate ligand and a ruthenium complex thereof, and preparation methods and applications of the ligand and the complex, and provides a ruthenium complex represented by a formula I, wherein L is a diaminodiphosphine tetradentate ligand represented by a formula II, and X and Y are respectively and independently chlorine ion, bromine ion, iodine ion,hydrogen negative ion or BH4. According to the present invention, the ruthenium complex exhibits excellent catalytic activity in the catalytic hydrogenation reactions of ester compounds, has high yield and high chemical selectivity, is compatible with conjugated and non-conjugated carbon-carbon double bond, carbon-carbon triple bond, epoxy, halogen, carbonyl and other functional groups, and hasgreat application prospects.