31610-67-0

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 172977-66-1 2,4,6-trimethylphenyl acrylate 
• 1772-43-6 2,4,4-trimethyl oxazoline 
• 7787-78-2 6-tert-Butyl-1-oxa-spiro[2.5]octane 
• 105-53-3 diethyl malonate 
• 10601-39-5 trans-(4-tert-butyl-cyclohexyl)-methanol 
• 10601-40-8 Toluolsulfonsaeure-(4)- 
• 943-29-3 trans-4-(tert-butyl)cyclohexane-1-carboxylic acid 
• 74-88-4 methyl iodide 
• 1380424-95-2 methyl 3-[(1r,4r)-4-(tert-butyl)cyclohexyl]propanoate 
• 2815-45-4 6-tert-butyl-1-oxaspiro[2.5]octane 
• 292638-85-8 acrylic acid methyl ester 
• 13004-07-4 Toluolsulfonsaeure-(4)- 
• 943-28-2 cis-4-t-butylcyclohexanecarboxylic acid 

Downstream Products

• 41732-97-2 4-tert-Butyl-1-(3-hydroxy-propyl)-cyclohexanol 
• 41732-96-1 4-tert-Butyl-1-(3-hydroxy-propyl)-cyclohexanol 

Relevant academic research and scientific papers

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.

SYNTHESIS OF 3-METHYLENE-1-OXA-8-HETERASPIRODECAN-2-ONES AND 1-OXA-8-HETERASPIRODECAN-2-ONES. NOVEL FORMATION AND CRYSTAL STRUCTURE OF 3--1-OXA-8-THIASPIRODECAN-2-ONE

A series of new 3-methylene-1-oxa-8-heteraspirodecan-2-ones have been prepared as the first members of the family.Reaction of 1-oxa-6-heteraspirooctanes with diethyl malonate, followed by hydrolysis, gave 3-carboxy-1-oxa-8-heteraspirodecan-2-ones.The carboxy lactone, upon treatment with diethylamine and formaldehyde followed by sodium acetate and acetic acid, produced α-methyl-eneheteraspiro lactones in good yields and in high purity.Moreover, the carboxy lactones could be decarboxylated smoothly to give 1-oxa-8-heteraspirodecan-2-ones in good yields.The present method appears to be superior to the widely used Reformatsky reaction since only low yields of the required lactones could be obtained when applied in the work reported herein.An investigation of dilithiated acetic acid as a co-reactant with spiro epoxides of heteracyclohexyl systems was undertaken but rather than the expected γ-lactones, unusual γ-hydroxylactones were obtained.Apparently, the anionic behavior of the dilithiated acetic acid caused the condensation to occur.All lactone systems were characterized via IR, 1H NMR and 13C NMR analysis and mass spectral data.A single crystal analysis by X-ray diffraction of 3--1-oxa-8-thiaspirodecane-2-one l2l2l, Z=4, a=5.916(2), b=11.585(3), c=21.986(5) Angstroem, T=138 K> was completed.Least-squares refinement converged to R=0.045 for 1319 diffractometer data.Both thiacyclohexyl rings are in the chair conformation and have C-O bonds which are axial.The sulfur ring with the hydroxyl group is orientationally disordered.This is the first example of such a fused heterocycle in which a structure of the crystal has been reported.