13030-92-7

Upstream product

• 7106-07-2 3,4,5,6,7,8-hexahydro-2H-chromene 
• 62456-11-5 2-(γ-Hydroxypropyl)-cyclohexanon 
• 108-94-1 cyclohexanone 
• 441049-09-8 1-hydroperoxy-2-oxabicyclo[4.4.0]decane 
• 98213-44-6 3-<(cyclohex-1-enyl)oxy>propan-1-ol 
• 84246-81-1 6-Nitro-9-nonanolide 

Relevant academic research and scientific papers

A new method for synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides

A new method for the synthesis of n-(3-acyloxypropyl)-substituted six- to thirteen-membered alkan-n-olides was developed. The method is based on the H2SO4-catalyzed reactions of oxabicycloalkenes, obtained from 2-(3-acetoxypropyl)cycloalkanes, with H2O2 and formic or acetic acid. The method includes the subsequent transformations of oxabicycloalkenes into bicyclic hydroperoxides, peroxy ethers, and, at the final stage, into target lactones formed in 56-71% yields. These transformations are carried as a one-pot reaction.

Ozonolysis of Enol Ethers. 9. Synthesis and Ozonolysis of 5,6,7,8-Tetrahydrochroman

The regioselectivity of the transfer of three oxygens of ozone to the olefinic carbons of the rigid substituted enol ether 5,6,7,8-tetrahydrochroman (3) is proved by isolation of ω-caprinolactone 5 instead of an earlier claimed oxacyclodecanone 4.

Highly Regio- and Stereo-selective Annulation-Elimination Reactions of 1-Cycloalkenyl 3-Hydroxypropyl Ethers

Highly regio- and stereo-selective annulation-elimination reactions of 1-cycloalkenyl 3-hydroxypropyl ethers in the presence of triflic anhydride and tertiary amines are described; the bicyclic vinyl ethers produced are converted to 2-substituted δ-lactones, macrocyclic oxolactones and bicyclic hydroxy ethers by ozonolysis and stereoselective hydroboration.

Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones by Cerium and Cyanoanthracene Catalysis

We describe a cerium-catalyzed aerobic oxidative ring expansion for the expedient construction of synthetically challenging macrolactones under visible-light conditions. Cyanoanthracene has been employed as co-catalyst to accelerate the turnover of the cerium cycle leading to a fast conversion within 20 min of irradiation. Taking advantage of the high efficiency and operationally simple conditions, a collection of over 100 macrolactones equipped with ring systems ranging from 9- to 19-membered macrocycles have been prepared from simple building blocks. Moreover, the enabling potential of this strategy to simplify the generation of molecular complexity has been demonstrated through the concise synthesis of sonnerlactone.

The photo-oxygenation of dihydropyrans. formation of 1,2-dioxetanes and 1,2,4-trioxanes

3,4-Dihydro-2H-pyran (1), 5,6,7,8-tetrahydrochroman (9), and 2-oxabicyclo[4.6.0]dodec-1(6)-ene (13) on dye-sensitized photo-oxygenation give the corresponding 1,2-dioxetanes (3), (10), and (14) in yields of 35-53% as isolable, stable entities with the exception of 10. 2-Hydroperoxy-5,6-dihydro-2H-pyran (5) is also obtained from 1 in 15% yield. No hydroperoxide is formed from 9, whereas 13 affords 3,4,6,7,8,9-hexahydro-2H-cycloocta[b]pyran-4a-yl hydroperoxide (15) in variable, but minor yields depending on the choice of solvent, temperature and sensitizer. Further [2 + 2] addition to 15 produces the 1,2-dioxetane (16). Repetition of the photo-oxygenation of 1, 9 and 13 in the presence of acetaldehyde affords the same products as before. In the case of 1, the cis-fused epimeric 1,2,4-trioxanes (7) are additionally formed in 2% yield. TMSOTf-catalyzed treatment of 3, 10, and 14 with acetaldehyde affords the corresponding 1,2,4-trioxanes in yields of 30, 30 and 43%. Thermolysis of 3, 10, and 14 breaks the dioxetane ring to produce the monocyclic keto lactones.

Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds

Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo(n.4.0)alkane, 2-oxabicyclo(n.4.0)alk-1(6)-ene and 2-oxabicyclo(n.4.0)alk-1(6+n)-ene is stereoselectivity synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent and tertiary amine). These compounds lead to polyfunctionalized cyclic compounds and some natural product. We propose that this annulation reaction proceeds through a pure S(N)2-like mechanism.

Pyridinium Chlorochromate in Organic Synthesis. A Facile and Selective Oxidative Cleavage of Enol Ethers

Pyridinium chlorochromate (PCC) has been found to be selective reagent for the oxidative cleavage of enol ethers to esters or keto lactones in high yields.

A NEW SYNTHESIS OF MACROCYCLIC KETO-LACTONES VIA RING EXPANSION OF 2-(3-HYDROXYPROPYL)-2-NITROCYCLOALKANONES

2-(3-Hydroxypropyl)-2-nitrocycloalkanones undergo base-catalysed isomerisation into nitro-lactones containing four more atoms in the ring, which can be smoothly converted to the corresponding keto-lactones.