182-01-4

Usage

InChI:InChI=1/C18H30O6/c1-4-10-16(11-5-1)19-21-17(12-6-2-7-13-17)23-24-18(22-20-16)14-8-3-9-15-18/h1-15H2

Upstream product

• 79-21-0 peracetic acid 
• 108-94-1 cyclohexanone 
• 2699-12-9 bis-(1-hydroperoxycyclohexyl)peroxide 
• 74897-52-2 1-(1-hydroxycyclohexyldioxy)-1-(1-hydroperoxycyclohexyldioxy)cyclohexane 
• 933-40-4 cycloxexanone dimethyl ketal 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 78-18-2 1-hydroxycyclohexyl 1-hydroperoxycyclohexyl peroxide 
• 2407-94-5 1,1'-dihydroxycyclohexyl peroxide 
• 202197-70-4 methyl 2-(4-oxopiperidin-1-yl)acetate 
• 2699-11-8 1,1-dihydroperoxycyclohexane 

Downstream Products

• 295-48-7 cyclopentadecane 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 109-29-5 15-hexadecanolide 
• 108-94-1 cyclohexanone 

Relevant academic research and scientific papers

Selective synthesis of cyclic triperoxides from 1,1′-dihydroperoxydi(cycloalkyl)peroxides and acetals using SnCl4

A method for the synthesis of 1,2,4,5,7,8-hexaoxonanes by the reaction of 1,1′-dihydroperoxydi(cycloalkyl)peroxides with acetals using SnCl4 has been developed. For the first time, it was shown that SnCl4 can serve as an effective reagent for the synthesis of cyclic organic peroxides. The proposed method allows obtaining 9-membered cyclic triperoxides selectively and in the yields of up to 90% based on the isolated product.

Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties

Starting from small cyclic ketones, continuous flow synthesis is used to produce medium-sized rings and macrocycles that are relevant for the fragrance industry. Triperoxides are important intermediates in this process and are pyrolyzed at temperatures above 250 °C. The synthesis is carried out in two continuously operated flow reactors connected by a membrane-operated separator. The practicality of flow chemistry is impressively demonstrated in this work by the use of hazardous reagent mixtures (30% H2O2, 65% HNO3) and the pyrolysis of no less problematic peroxides. All new macrocycles were tested for their olfactory properties in relation to musk.

Method for preparing macrolide precursor

The invention belongs to the technical field of organic synthesis and particularly discloses a method for preparing a macrolide precursor. The method comprises the following steps: (1) mixing cyclohexanone and hydrogen peroxide, further adding a ferric salt catalyst, carrying out a reaction for 1-8 hours at the room temperature, and carrying out column chromatography separation after the reactionis completed so as to obtain a main product 1,1'-dihydroperoxide dicyclohexyl peroxide; (2) condensing the main product with cyclohexanone under catalysis of an organic acid, and after the reaction ends, carrying out separation and purification, thereby obtaining the macrolide precursor 1,2,4,5,7,8-hexaoxa-3,6,9-tricyclohexylidene cyclononane. The cyclohexanone which is low in price and easy to obtain is adopted as a raw material, and the product is prepared through two steps of reactions under catalysis of a ferric salt and a small amount of the organic acid at 20-45 DEG C; the method is simple and convenient in process, high in yield, applicable to popularization and application, and the product prepared by using the method can be applied to fields such as a cigarette fixative agent.

Unique trifurcated hydrogen bonding in a pseudopolymorph of tricyclohexane triperoxide (TCTP) and its thermal studies

Tricyclohexane triperoxide (TCTP) was synthesized as a main by-product of tetraoxane synthesis and was characterized by spectroscopic techniques viz. 1H NMR, 13C NMR, FT-IR and Raman. The single crystal X-ray structure revealed the inclusion of solvent in 1:1 stoichiometric ratio involving a unique trifurcated C(sp3)-H...O hydrogen bonding imparting remarkable symmetry to the molecule. The thermal stability of single crystal was determined by TG-DTA and DSC.

Reaction of enol ethers with the I2-H2O2 system: Synthesis of 2-iodo-1-methoxy hydroperoxides and their deperoxidation and demethoxylation to 2-iodo ketones

The reaction of enol ethers with the I2-H2O 2 system in diethyl ether affords 2-iodo ketones and the previously unknown 2-iodo-1-methoxy hydroperoxides. In the presence of the I 2-H2O2 system, the latter compounds undergo deperoxidation and demethoxylation to form 2-iodo ketones. The reaction conditions were found for the synthesis of 2-iodo ketones from enol ethers in 67-94% yields. Georg Thieme Verlag Stuttgart - New York.

New preparation of 1,2,4,5,7,8-hexaoxonanes

(Chemical Equation Presented) A new versatile procedure was developed for the synthesis of 1,2,4,5,7,8-hexaoxonanes based on the Lewis acid catalyzed reaction of acetals with 1,1′-dihydroperoxydicycloalkyl peroxides. The procedure substantially extends the structural diversity of these compounds and, in most cases, allows the synthesis of these compounds in higher yields (to 96%) and with higher selectivity. Complexation of hexaoxonane with chloroform was documented for the first time. The structures of several triperoxides were established by X-ray diffraction.

METHOD FOR THE PRODUCTION OF TRIMERIC KETONE PEROXIDE SOLUTIONS

Cyclohexanone is reacted with hydrogen peroxide in the presence of nitric acid which is used as a catalyst in a suitable solvent for the production of trimeric cyclohexanone peroxide.

Ketone-derived Peroxides. Part I. Synthetic Methods.

Study of the reactivity of peroxides derivable from ketones by reaction with hydrogen peroxide has required reexamination of preparative methods.Conditions for obtaining five known peroxides from cyclohexanone and the new 1-(1-hydroxycyclohexyldioxy)-1-(1-hydroperoxycyclohexyldioxy)cyclohexane (10) are carefully defined.An improved general method for obtaining cyclic diperoxides (3,3,6,6-tetrasubstituted 1,2,4,5-tetraoxans) (6) has been developed and used to obtain new diperoxides from dibenzyl ketone, di-(4-methylbenzyl) ketone and 2,2-dimethylcyclohexanone whereas indan-2-one and 5,7-dihydro-6H-dibenzocyclohepten-6-one yield the corresponding triperoxides (1,2,4,5,7,8-hexoxonans) (7) and 1,5-diphenylpentan-3-one yields bis-(1-hydroperoxy-1-phenethyl-3-phenylpropyl) peroxide (5k).Ozonolysis of appropriate alkenes has been used to obtain new cyclic diperoxides formally related to 4'-methylacetophenone, propiophenone and deoxybenzoin.