176-32-9

Usage

InChI:InChI=1/C7H12O2/c1-2-4-7(3-1)8-5-6-9-7/h1-6H2

Upstream product

• 107-21-1 ethylene glycol 
• 120-92-3 cyclopentanone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 75-21-8 oxirane 

Downstream Products

• 563-80-4 3-methyl-butan-2-one 
• 183-03-9 1,4-dioxaspiro<4.7>dodecane 
• 120-92-3 cyclopentanone 
• 376-66-9 perfluorocyclopentanone 
• 485318-53-4 endo-2,4-dibromodicyclopentadiene-1,8-dione 1,8-bis(ethylene acetal) 
• 485318-53-4 endo-2,4-dibromodicyclopentadiene-1,8-dione bisethylene ketal 
• 86587-56-6 2-cyclopentyloxyethyl 4-toluenesulphonate 
• 29412-62-2 cubane-1,4-dicarboxylic acid dimethyl ester 
• 32846-66-5 cubane-1,4-dicarboxylic acid 
• 32846-64-3 (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione 
• 485318-53-4 (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal 
• 1354967-16-0 C₂₅H₃₅N₃O₆ 
• 1354967-15-9 1-(2-(3-(4-(2-(cyclopentyloxy)ethoxy)phenoxy)-2-hydroxypropylamino)ethyl)-3-(3-hydroxyphenyl)urea 
• 1354967-14-8 1-(2-(3-(4-(2-(cyclopentyloxy)ethoxy)phenoxy)-2-hydroxypropylamino)ethyl)-3-(2-hydroxyphenyl)urea 

Relevant academic research and scientific papers

Acidic properties of sulfonic acid-functionalized FSM-16 mesoporous silica and its catalytic efficiency for acetalization of carbonyl compounds

Propyl-sulfonic acid-functionalized FSM-16 mesoporous silica (SO 3H-FSM) is prepared by a conventional post-modification method. For the acetalization of carbonyl compounds with ethylene glycol, SO 3H-FSM shows a higher rate and 1,3-dioxolane yield than conventional heterogeneous solid acids such as zeolites, montmorillonite K10 clay, silica-alumina, and the sulfonic resin. SO3H-FSM is stable during the reaction, with no leaching and deactivation of sulfonic acid groups, and is reusable without loss of its activity. The acidity and hydrophilicity of SO 3H-FSM are well characterized by the microcalorimetry of NH 3 adsorption, NH3-TPD, and H2O-TPD, and the result is compared with those for various aluminosilicate zeolites (HZSM5, HBEA, HY) and K10 clay. It is found that NH3-TPD is not suitable for characterizing the acidity of SO3H-FSM, because the decomposition of SO3H groups on SO3H-FSM begins above 200°C. An NH 3 adsorption microcalorimetric experiment at 150°C shows that, compared with HZSM5, SO3H-FSM has a smaller number of acid sites but has a similar number of strong acid sites with ammonia adsorption heat above 140 kJ mol-1. Comparison of the structural properties and catalytic results shows that a large pore diameter and low hydrophilicity are required to obtain high activity. Bronsted acid sites with a relatively strong acid strength are more suitable for this reaction, but the high acid concentration is not indispensable. The high activity of SO3H-FSM should be caused by the presence of the strong Bronsted acid sites in the mesopore with a relatively low hydrophilicity, where both reactants can smoothly access the acid sites.

A green procedure for the protection of carbonyl compounds catalyzed by iodine in ionic liquid

Aldehydes and ketones are protected with ethylene glycol in the presence of a catalytic amount of iodine in PEG ionic liquid (IL 400) under mild conditions to afford the corresponding ketals in good yields. The recovery of iodine is facilitated by the ionic liquid. The recovered catalyst was reused six times with consistent activity.

Highly efficient heterogeneous acetalization of carbonyl compounds catalyzed by a titanium cation-exchanged montmorillonite

The titanium cation-exchanged montmorillonite efficiently catalyzed the selective acetalization of various carbonyl compounds as a recyclable solid acid. This heterogeneous catalyst has an advantage of a strikingly simple workup procedure over conventional homogeneous acids.

Synthesis of a novel chiral cubane-based Schiff base ligand and its application in asymmetric nitro-aldol (Henry) reactions

The first reported cubane-based chiral Schiff base ligand has been successfully synthesized. This ligand has been evaluated on the nitro-aldol (Henry) reaction. The reactions were performed in the presence of four different copper salts, using eight different solvents, and five different temperatures. The highest enantioselectivity obtained for this novel ligand was ～39% ee.

Correlation between 13C and 17O chemical shifts and torsional strain in spiroacetals

The relationship between the 13C and 17O NMR chemical shifts and the dihedral energies (non-bonding interactions) of 1,4-dioxaspiro[4.4]nonane, 1,4-dioxa- and 6,10-dioxaspiro[4.5]decane, 1,4-dioxa- and 6,11-dioxaspiro[4.6]undecane, 1,5-dioxaspiro[5.5]undecane, 1,5-dioxa and 7,12-dioxaspiro[5.6]dodecane and 1,6-dioxaspiro[6.6]tridecane were analyzed. These data showed correlation of the non-bonding interactions with the chemical shift of the spiranic carbon, as well as a linear relationship between 13C and 17O.

Decagram Synthesis of Dimethyl 1,4-Cubanedicarboxylate Using Continuous-Flow Photochemistry

The highly strained cubane system is of great interest as a scaffold and rigid linker in both pharmaceutical and materials chemistry. A straightforward approach is reported for the scale-up of a [2+2] photocycloaddition step using convenient home-made flow photoreactors to access dimethyl 1,4-cubanedicarboxylate on decagram-scale in 33-40% yield over 8 steps. The process is demonstrated on 3.4 g·h -1input with 30 minutes residence time, enabling to reduce the process time and to avoid the use of batch photoreactors. Completion of the characterisation of the photocycloadduct and its hydrates is reported.

Thermochemical properties of iodinated cubane derivatives

Since the initial synthesis of cubane, numerous derivatives have been made with a diverse range of physical, chemical, and biological properties. Some iodinated cubane derivatives have been reported to be thermolytically unstable and/or rearrange in situ. An iodinated cubane-containing, norbornene-based polymer showed rapid thermo-decomposition during TGA studies. Bis-(4-iodocubylmethyl)-dialkoxy disulfide undergoes fragmentation more easily than its non-iodinated counterpart. The synthesis and thermal behaviour of a library of iodinated cubane compounds are herein reported. Most of the iodinated cubane derivatives showed melting/decomposition with no exotherm upon cooling. 4-Iodo-1-vinylcubane was observed to rearrange to 4-vinyl-trans-β-iodostyrene and its cyclooctatetraene intermediate during DSC analysis. TGA studies on 1-iodo-4-(hydroxymethyl)-cubane suggest that this particular iodinated cubane scaffold is mostly prone to rapid thermo-decomposition.

Eco-friendly Pt-Mo/ZrO2 solid acid catalyst for selective protection of carbonyl compounds

An easy method for protection of carbonyl compounds has been carried out in excellent yields under catalysis of Pt-Mo/ZrO2 in toluene at 383 K.

Microwave-assisted acetalization of carbonyl compounds catalyzed by reusable Envirocat supported reagents

Envirocat supported reagents (EPZG, EPZ10, and EPIC) are found to efficiently catalyze the acetalization of carbonyl compounds with 1,2-ethanediol under microwave irradiation under solvent-free conditions. The reagents can be used in repeated experiments to perform the reaction with the same activity.

Green efficient synthesis of ketal under catalysis of ionic liquid TTPT

The invention discloses a method for green efficient synthesis of ketal under catalysis of ionic liquid TTPT. The method comprises the following steps: adding TTPT and a water-carrying agent into a raw material I and a raw material II, and carrying out a heating reflux reaction for 110-150 minutes, wherein R1 and R2 in formulas I and II are independently selected from a group consisting of a methyl group, an ethyl group and a phenyl group, or R1 and R2 are connected and cyclized to form a 5-to-10-membered naphthenic base; and R3 is selected from H or-OH. Compared with the prior art, the catalytic yield of the TTPT is remarkably improved, a good catalytic effect is achieved, and experimental operation is easy and convenient.