17844-23-4

Usage

Uses

Used in Perfume Industry:
5-Hexen-1-ol, 4-methyleneis used as an intermediate in the manufacturing of perfume chemicals for creating fragrant compounds that contribute to the unique scents of various perfumes.
Used in Synthesis of β-Myrcene-d6:
5-Hexen-1-ol, 4-methyleneis also utilized as an intermediate in the synthesis of β-Myrcene-d6 (M875302), which is a deuterated version of β-myrcene, a naturally occurring terpene found in many plants. 5-Hexen-1-ol, 4-methyleneis used in various applications, including research and development in the chemical and pharmaceutical industries.

Upstream product

• 75-21-8 oxirane 
• 108-18-9 diisopropylamine 
• 78-79-5 isoprene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 150255-70-2 tert-butyldimethyl((4-methylenehex-5-en-1-yl)oxy)silane 
• 17844-21-2 4-methylene-5-hexenal 
• 5390-04-5 pent-1-yn-5-ol 
• 61362-77-4 5-[tert-butyldimethylsilyloxy]pent-1-yne 
• 157-18-6 oxirene 

Downstream Products

• 141621-48-9 (E)-7,7-Bis-benzenesulfonyl-4-methyl-hept-4-en-1-ol 
• 141621-49-0 (E)-4-(2,2-Bis-benzenesulfonyl-ethyl)-hex-4-en-1-ol 
• 818-49-5 4-methylhexan-1-ol 

Relevant academic research and scientific papers

Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes

A family of single-component iron precatalysts for the [4+4]-cyclodimerization and intermolecular cross-[4+4]-cycloaddition of monosubstituted 1,3-dienes is described. Cyclooctadiene products were obtained with high regioselectivity, and catalyst-controlled access to either cis- or trans-diastereomers was achieved using 4-substituted diene substrates. Reactions conducted either with single-component precatalysts or with iron dihalide complexes activated in situ proved compatible with common organic functional groups and were applied on multigram scale (up to >100 g). Catalytically relevant, S = 1 iron complexes bearing 2-(imino)pyridine ligands, (RPI)FeL2 (RPI = [2-(2,6-R2-C6H3-Na-CMe)-C5H4N] where R = iPr or Me, L2 = bis-olefin), were characterized by single-crystal X-ray diffraction, M??bauer spectroscopy, magnetic measurements, and DFT calculations. The structural and spectroscopic parameters are consistent with an electronic structure description comprised of a high spin iron(I) center (SFe = 3/2) engaged in antiferromagnetically coupling with a ligand radical anion (SPI = -1/2). Mechanistic studies conducted with these single-component precatalysts, including kinetic analyses, 12C/13C isotope effect measurements, and in situ M??bauer spectroscopy, support a mechanism involving oxidative cyclization of two dienes that determines regio- and diastereoselectivity. Topographic steric maps derived from crystallographic data provided insights into the basis for the catalyst control through stereoselective oxidative cyclization and subsequent, stereospecific allyl-isomerization and C-C bond-forming reductive elimination.

Towards a Supertough Thermoplastic Polyisoprene Elastomer Based on a Biomimic Strategy

Natural rubber is one of most famous self-reinforced rubbers thanks to the phenomenon of strain-induced crystallization. It is usually used in a vulcanized form to enhance the mechanical strength but this results in recycling issues. Herein a thermoplastic analogue of vulcanized natural rubber is obtained as a structural mimic. Terminally functionalized polyisoprene rubber B-4A-PIP was prepared by using tetra-analine as physical crosslinking units. The strong binding of tetra-analine groups gave B-4A-PIP a high tensile strength (15 MPa) and breaking strain of 890 %, which is much higher than those of undecorated copolymer B-OH-PIP. B-4A-PIP has a similar onset strain of crystallization and crystallization index to vulcanized natural rubber. Randomly functionalized polyisoprene R-4A-PIP showed a much lower mechanical strength and SIC properties although R-4A-PIP and B-4A-PIP possessed similar molecular weights and amounts of tetra-analine groups.

Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines

A Cu-catalyzed diastereo- and enantioselective borylative coupling reaction of 1,3-dienes with imines was realized. Branched homoallylic amines are readily prepared in a syn-selective manner with high regio-, diastereo- and enantioselectivity. Moreover, t

Assessment of catalysis by arene-ruthenium complexes containing phosphane or NHC groups bearing pendant conjugated diene systems

Two p-cymene-ruthenium complexes 1 and 2 were isolated in high yields by treating the [RuCl2(p-cymene)]2 dimer with new hybrid phosphane- or NHC-linked diene ligands. Both complexes were fully characterized by NMR spectroscopy, and the molecular structure of the ruthenium-p-cymene complex 1, containing the phosphane-diene ligand system, was determined by X-ray diffraction analysis. The catalytic activities of both compounds were probed in atom-transfer radical addition (ATRA) and polymerization (ATRP), in the cyclopropanation of olefins, in the ring-opening metathesis polymerization (ROMP) of norbornene, and in the synthesis of enol esters from hex-1-yne and 4-acetoxybenzoic acid.

Microwave assisted synthesis of bridgehead alkenes

A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels-Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter

Iron-catalyzed 1,4-hydroboration of 1,3-dienes

(Chemical Equation Presented) A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords γ-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.

Dual function catalysts. Dehydrogenation and asymmetric intramolecular Diels-Alder cycloaddition of N-hydroxy formate esters and hydroxamic acids: Evidence for a ruthenium-acylnitroso intermediate

The chiral ruthenium salen complex, 13b, functions as an efficient catalyst for the sequential oxidation and asymmetric Diels-Alder cycloaddition of hydroxamic acids and N-hydroxy formate esters. This result provides evidence for the formation of a ruthen

Bridged to fused ring interchange. Methodology for the construction of fused cycloheptanes and cyclooctanes. Total syntheses of ledol, ledene, and compressanolide

The type two intramolecular Diels-Alder reaction (T2IMDA) is an efficient method for the formation of medium rings. The methodology is particularly effective for the construction of seven- and eight-membered rings. A strategy for the synthesis of functionalized cycloheptanes and cyclooctanes has been developed that involves a bridged to fused ring interchange. The T2IMDA provides a synthesis for rigid bridged bicyclic molecules that can be stereoselectively elaborated before ozonolysis of the bridgehead double bond. Following oxidative cleavage, aldol condensation provides fused bicyclic ring systems that otherwise are difficult to synthesize. This methodology is amenable to the synthesis of terpene natural products. This is demonstrated here through total syntheses of (±)-ledol and (±)-ledene and a formal synthesis of (±)-compressanolide.

ON THE DIRECT METALATION OF ISOPRENE

Isoprene has been metalated in tetrahydrofuran with an excess of sterically hindered potassium dialkylamides, prepared by combining equimolar amounts of the corresponding lithium amide and potassium tert-butoxide.Subsequent reaction with oxirane, alkyl bromides, and pivaldehyde gave the expected coupling products in reasonable yields.Coupling with (CH3)2CHCH2CH=O and (CH3)2C=CHCH=O afforded the bark beetle pheromones (+/-)-ipsenol and (+/-)-ipsdienol in low yields.

Direct Metallation of Isoprene

Treatment of isoprene with an excess of the couple potassium t-butoxide-lithium tetramethylpiperidine in tetrahydrofuran, followed by addition of a higher alkyl bromide or oxirane, gives the dienes H2C=CHC(=CH2)CH2R (R = alkyl or -CH2CH2OH) in reasonable yields.