5057-99-8

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL is used as a building block for the synthesis of chiral phosphine ligands, which are essential in the development of enantioselective catalysts. These catalysts play a crucial role in the production of pharmaceuticals, as they enable the selective synthesis of specific enantiomers with desired biological activity.
Used in Chemical Synthesis:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL is used as a precursor in the preparation of benzoquinolines and benzoindoles. These heterocyclic compounds are synthesized through the heterocyclization of naphthylamines with diols, catalyzed by iridium chloride/BINAP. Benzoquinolines and benzoindoles are valuable intermediates in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.

InChI:InChI=1/C5H10O2/c6-4-2-1-3-5(4)7/h4-7H,1-3H2

Upstream product

• 3008-40-0 cyclopentane-1,2-dione 
• 29974-65-0 1,2-dibromo-cyclopentane 
• 29782-81-8 (+/-)-trans-cyclopentene-⁽¹⁾-diol-(3.4) 
• 142-29-0 cyclopentene 
• 285-67-6 Cyclopentene oxide 
• 99440-98-9 2-hydroxycyclopentanone 
• 7722-84-1 dihydrogen peroxide 
• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 287-92-3 Cyclopentane 
• 542-92-7 cyclopenta-1,3-diene 
• 96-41-3 Cyclopentanol 
• 111-30-8 Glutaraldehyde 

Downstream Products

• 111-30-8 Glutaraldehyde 
• 930-46-1 (1R,2R)-cyclopentane-1,2-diol 
• 63261-45-0 (S,S)-cyclopentane-1,2-diol 
• 99493-88-6 (R)-2-hydroxycyclopentanone 
• 126508-02-9 (+/-)-2,4-Diphenyl-(5ar,8at)-tetrahydro-cyclopenta[1,3,5,2,4]trioxadiborepin 
• 133442-59-8 (R,R)-1,2-diacetoxycyclopentane 
• 20520-67-6 (S,S)-2-acetoxycyclopentan-1-ol 
• 285-67-6 Cyclopentene oxide 
• 110-94-1 1,5-pentanedioic acid 
• 34267-03-3 di(p-nitrobenzoate) de cyclopentanediol-1,2 trans 
• 37844-60-3 p-nitrobenzoate d'hydroxy-2 cyclopentyle trans 
• 15051-88-4 trans-cyclopentane-1,2-diol 1-tosylate 
• 7462-36-4 trans-1,2-cyclopentanediol phenylboronic ester 
• 20520-67-6 (1R,2R)-2-hydroxycyclopentyl acetate 

Relevant academic research and scientific papers

Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water

Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

Preparation of Highly Active Monometallic Rhenium Catalysts for Selective Synthesis of 1,4-Butanediol from 1,4-Anhydroerythritol

1,4-Butanediol can be produced from 1,4-anhydroerythritol through the co-catalysis of monometallic mixed catalysts (ReOx/CeO2+ReOx/C) in the one-pot reduction with H2. The highest yield of 1,4-butanediol was over 80 %, which is similar to the value obtained over ReOx–Au/CeO2+ReOx/C catalysts. Mixed catalysts of CeO2+ReOx/C showed almost the same performance, giving 89 % yield of 1,4-butanediol. The reactivity trends of possible intermediates suggest that the reaction mechanism over ReOx/CeO2+ReOx/C is similar to that over ReOx–Au/CeO2+ReOx/C: deoxydehydration (DODH) of 1,4-anhydroerythritol to 2,5-dihydrofuran over ReOx species on the CeO2 support with the promotion of H2 activation by ReOx/C, isomerization of 2,5-dihydrofuran to 2,3-dihydrofuran catalyzed by ReOx on the C support, hydration of 2,3-dihydrofuran catalyzed by C, and hydrogenation to 1,4-butanediol catalyzed by ReOx/C. The reaction order of conversion of 1,4-anhydroerythritol with respect to H2 pressure is almost zero and this indicates that the rate-determining step is the formation of 2,5-dihydrofuran from the coordinated substrate with reduced Re in the DODH step. The activity of ReOx/CeO2+ReOx/C is higher than that of ReOx–Au/CeO2+ReOx/C, which is probably related to the reducibility of ReOx/C and the mobility of the Re species between the supports. High-valent Re species such as Re7+ on the CeO2 and C supports are mobile in the solvent; however, low-valent Re species, including metallic Re species, have much lower mobility. Metallic Re and cationic low-valent Re species with high reducibility and low mobility can be present on the carbon support as a trigger for H2 activation and promoter of the reduction of Re species on CeO2. The presence of noble metals such as Au can enhance the reducibility through the activation of H2 molecules on the noble metal and the formation of spilt-over hydrogen over noble metal/CeO2, as indicated by H2 temperature-programmed reduction. The higher reducibility of ReOx–Au/CeO2 lowers the DODH activity of ReOx–Au/CeO2+ReOx/C in comparison with ReOx/CeO2+ReOx/C by restricting the movement of Re species from C to CeO2.

Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons

A transition-metal-free cis-dihydroxylation of saturated hydrocarbons under ambient reaction conditions has been developed. The described approach allows a direct and selective synthesis of vicinal diols. The new reaction thereby proceeds via radical iodination and a sequence of oxidation steps. A broad scope of one-pot dual C(sp3)-H bond functionalization for the selective synthesis of vicinal syn-diols was demonstrated.

Bronsted acid-catalyzed dihydroxylation of olefins in aqueous medium

The trans-dihydroxylation of olefins occurs efficiently by aqueous hydrogen peroxide catalyzed by p-toluenesulfonic acid at 50°C, allowing the catalyst reuse and an outstanding substrate functional group tolerance such as tert-butoxycarbonylamino (BocNH), benzyloxycarbonylamino (CbzNH), benzyloxy (OBn), tosyloxy (OTs), hindered ketal, (2-trimethylsilyl)ethoxymethoxy (OSEM), benzylamino (NBz), benzyloxy (OBz) and free amino acid. Copyright

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

Carbon tetrabromide: An efficient catalyst for regioselective ring opening of epoxides with alcohols and water

Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity. Georg Thieme Verlag Stuttgart.

Tetrabutylammonium bisulfate: A new effective catalyst for the hydrolysis of aziridines or epoxides

Bu4NHSO4 (TBAHS) is an effective catalyst for the hydrolysis of aziridines and epoxides under mild and non-metal conditions to give the corresponding β-amino alcohols and 1,2-diols in high yields. The catalyst can be recycled.

One-Pot and Stereospecific Synthesis of cis-1,2-Diazides via Mitsunobu Reaction of Epoxides

Mitsunobu reaction of epoxides using hydrazoic acid, diethylazodicarboxylate, and triphenylphosphine as reagents gave the corresponding cis-1,2-diazides in moderate yield. Application of similar reaction conditions to trans-diols furnished the corresponding trans-1,2-diazides.

Selective oxidation of cyclopentene to glutaraldehyde by H2O2 over the WO3/SiO2 catalyst

A novel WO3/SiO2 was prepared by incipient wetness impregnation of the SiO2 support synthesized by the xerogel method with the W-containing salt solution. The as-prepared WO3/SiO2 catalyst exhibited a very high yield of glutaraldehyde in the liquid phase cyclopentene oxidation by aqueous H2O2 and the leach of WO3 species during the reaction could be neglected. As a heterogeneous catalyst, it seems more suitable for the industrial process than those homogeneous catalysts owing to its easy separation from reaction products, which makes it possible to use the catalyst repetitively. According to the XRD patterns, the WO3 was present in amorphous state due to its high dispersion on the SiO2 support. These amorphous WO3 species were proved to be the active sites since the crystallization at high temperature caused a considerable deactivation. The lifetime of the catalyst was measured and its regeneration method was proposed. Effects of various factors on the catalytic behaviors, such as the WO3 loading, the calcination temperature, and the reaction media, were also investigated and discussed based on the characterizations of BET, XRD, DSC, TEM, EXAFS, and Raman spectra.