72258-83-4

Usage

InChI:InChI=1/C13H22O2/c1-12(2,3)10-4-7-13(8-5-10)9-6-11(14)15-13/h10H,4-9H2,1-3H3

Upstream product

• 72252-03-0 (+/-)-2-(1-ethoxyethoxy)-but-3-enenitrile 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 104089-16-9 2-ethoxycarbonyethylzinc iodide 
• 140-88-5 ethyl acrylate 
• 13294-73-0 1-tert-butyl-4-methylenecyclohexane 
• 623-48-3 ethyl iodoacetae 
• 172977-66-1 2,4,6-trimethylphenyl acrylate 
• 537033-32-2 8-tert-butyl-1-oxa-spiro[4.5]decan-2-ol 
• 292638-85-8 acrylic acid methyl ester 
• 2815-45-4 6-tert-butyl-1-oxaspiro[2.5]octane 
• 1380424-93-0 C₁₄H₂₆O₂ 
• 1380424-74-7 3-[(1s,4s)-4-(tert-butyl)cyclohexyl]propanoic acid 
• 13004-06-3 cis-(4-tert-butylcyclohexyl)methanol 
• 943-28-2 cis-4-t-butylcyclohexanecarboxylic acid 

Downstream Products

• 41732-96-1 4-tert-Butyl-1-(3-hydroxy-propyl)-cyclohexanol 
• 41732-97-2 4-tert-Butyl-1-(3-hydroxy-propyl)-cyclohexanol 
• 307924-98-7 (+/-)-3-[4(tert-butyl)cyclohex-1-en-1-yl]propanal 
• 766537-98-8 6-(tert-butyl)-2,3,4,5,6,7-hexahydro-1H-inden-1-one 
• 766537-94-4 3-[4(tert-butyl)cyclohex-1-en-1-yl]propanoic acid 

Relevant academic research and scientific papers

Methyl Radical Initiated Kharasch and Related Reactions

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).

Directed metal (oxo) aliphatic C-H hydroxylations: Overriding substrate bias

The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

The stereochemistry of electrolysis and samarium diiodide-induced cyclization between carbonyl and enone system in inter- and intramolecular coupling

Both the inter- and intramolecular cyclization of the carbonyl compounds with α,β-unsaturated carbonyl system using samarium diiodide and electrolysis were carried out. The stereochemistry of the products was compared each other.

Synthesis of new furan derivatives and 4-hydroxy aldehydes from 4-hydroxy 1-enol ethers

Starting from 4-hydroxy 1-enol ethers 3 different γ-lactols 4 were successfully prepared by acidic hydrolysis. Subsequent oxidation of 4 with pyridinium chlorochromate (PCC) led to γ-lactones 6 in good to excellent overall yields. Treatment of γ-lactols 4

Samarium diiodide-induced couplings of carbonyl compounds with methoxyallene leading to 4-hydroxy 1-enol ethers

(Matrix presented) A surprising samarium diiodide-induced coupling reaction of carbonyl compounds with methoxyallene provided 4-hydroxy 1-enol ethers, which are versatile synthetic building blocks. In this coupling reaction, methoxyallene serves as an acrolein equivalent, which cannot directly be employed.

Spiro γ-lactones via aluminum enolate-spiroepoxide openings

The opening of several spiroepoxides by aluminum ester enolates is described. The isolated γ-hydroxy esters are cyclized to the corresponding spirolactones with high efficiency. Alternatively, the crude product from epoxide opening may be directly converted to the spirolactone without purification of the intermediate hydroxy ester. This methodology provides another complementary route to 1-oxaspiro[4.n]-2-one systems that are of structural and biological interest.

Catalytic reactions of samarium(II) iodide

A system for in situ regeneration of SmI2 from SmI3 is described which allows the annulation of ketones to γ-lactones, the deoxygenation of oxiranes to olefins and radical π-cyclization to be conducted with 10 mole % SmI2.

Samarium(II) Di-iodide Induced Reductive Coupling of α,β-Unsaturated Esters with Carbonyl Compounds Leading to a Facile Synthesis of γ-Lactone

Samarium(II) di-iodide, which is a strong one-electron transfer reducing agent, is effective for the reductive coupling of α,β-unsaturated esters with carbonyl compounds, whereby substituted γ-lactones can easily be prepared in good to excellent yields under very mild conditions.Two mole equiv. of samarium(II) di-iodide to each mole equiv. of starting substrate always give reasonable yields.The presence of an alcohol is essential in the reaction, complex unidentified products being formed in the absence of an alcohol; t-butyl alcohol gave more satisfactory results than methanol and ethanol.The alcohol acts as a proton donor, the use of MeOD leading to a deuteriated γ-lactone.The reaction is applicable to both aliphatic and aromatic ketones or aldehydes, whereas the electrochemical method is limited to aliphatic substrates.The diastereoselectivity is examined in the reaction of 4-t-butylcyclo-hexanone with ethyl acrylate; an anti-isomer is produced predominantly (syn:anti = 1:9) as the result of selective axial attack.The reaction may proceed by a radical mechanism, and reaction may not involve a samarium ester homoenolate.The reaction is extended to the intramolecular reaction of an α,β-unsaturated keto ester (8-oxonon-2-enoate) leading to the ready synthesis of a bicyclic γ-lactone.

Spirolactones as odorants

Fragrance compositions comprising 8-alkyl-1-oxaspiro[4.5]decan-2-ones wherein the alkyl group contains from one to four carbon atoms.