86703-52-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Production:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL is used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its ability to create complex molecules with specific stereochemistry.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, (+/-)-TRANS-1,2-CYCLOPENTANEDIOL serves as a chiral auxiliary, aiding in the production of enantiomerically pure compounds, which is crucial for the development of effective and selective drugs.
Used as a Reagent in Chemical Reactions:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL is also employed as a reagent in various chemical reactions, contributing to the synthesis of different types of molecules and compounds.
Used in the Development of Novel Materials:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL has shown potential in the development of novel materials, which could lead to advancements in various industries.
Used in Organic Electronics:
(+/-)-TRANS-1,2-CYCLOPENTANEDIOL may have applications in the field of organic electronics, where its unique structure and properties could contribute to the creation of innovative electronic devices and components.

Upstream product

• 5057-99-8 trans-cyclopentane-1,2-diol 
• 20520-67-6 (1R,2R)-2-hydroxycyclopentyl acetate 
• 135357-03-8 trans-1-Phenoxy-cyclopentanol-⁽²⁾ 
• 26620-22-4 (+/-)-trans-1,2-diacetoxycyclopentane 
• 113625-73-3 (1R,2R)-(-)-2-benzyloxycyclopentanol 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 285-67-6 (1S,5R)-6-Oxa-bicyclo[3.1.0]hexane 
• 78823-36-6 p-nitrobenzoic-propionic anhydride 
• 97-72-3 2-Methylpropionic anhydride 
• 694-29-1 (+/-)-cis-Cyclopent-3-ene-1,2-diol 
• 20520-67-6 (+/-)-cis-1-acetoxy-2-hydroxycyclopentane 
• 10230-26-9 trans-1,2-dibromocyclopentane 
• 563-63-3 silver(I) acetate 

Downstream Products

• 109017-73-4 2ξ-phenoxy-(3ar,6ac)-tetrahydro-cyclopenta[1,3,2]dioxaphosphole 
• 15051-88-4 cis-2-hydroxycyclopentyl 4-toluenesulfonate 
• 876605-79-7 cis-1,2-bis-(toluene-4-sulfonyloxy)-cyclopentane 
• 37854-34-5 cis-1,2-Di-(p-methoxybenzoyloxy)-cyclopentan 
• 579-21-5 Lobelanine 
• 930-46-1 (1R,2R)-cyclopentane-1,2-diol 
• 63261-45-0 (S,S)-cyclopentane-1,2-diol 
• 1532564-68-3 C₈H₁₄O₃ 

Relevant academic research and scientific papers

Magnesium chloride-catalyzed thiolysis of epoxides: Synthesis of β-hydroxy sulfides

A mild and convenient ring opening of epoxides with thiophenol and its derivatives takes place at room temperature in the presence of magnesium chloride as catalyst to afford the corresponding β-hydroxy sulfides along with minor amounts of 2-chlorocycloalkanols in good yields. When the crude reaction mixtures are treated with aqueous sodium hydroxide solution, pure 2-arlythiocycloalkanols are obtained in good yields.

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols

Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under

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.

Oxidative cleavage of cycloalkenes using hydrogen peroxide and a tungsten-based catalyst: Towards a complete mechanistic investigation

The identification of the intermediates and by-products produced during the oxidative cleavage of cycloalkenes in the presence of H2O2 and a tungsten-based catalyst for the production of dicarboxylic acids has been carried out under various experimental conditions. On the basis of this mechanistic investigation and previous studies from the literature, a complete reaction scheme for the formation of the reaction products and by-products is proposed. In this hypothetical mechanism, the production of a hydroperoxyalcohol intermediate accounts for the two pathways proposed by Noyori and Venturello for the formation of the targeted dicarboxylic acid. In addition, Baeyer-Villiger oxidation of the mono-aldehyde intermediate allows explaining the formation of short chain diacids observed as by-products during the reaction. Hence, the proposed mechanism constitutes a real tool for scientists looking for a better understanding and those heading to set up environmentally friendly conditions for the oxidative cleavage of cycloalkenes.

Tandem Lewis acid catalysis for the conversion of alkenes to 1,2-diols in the confined space of bifunctional TiSn-Beta zeolite

The generation of multifunctional isolated active sites in zeolite supports is an attractive method for integrating multistep sequential reactions into a single-pass tandem catalytic reaction. In this study, bifunctional TiSn-Beta zeolite was prepared by a simple and scalable post-synthesis approach, and it was utilized as an efficient heterogeneous catalyst for the tandem conversion of alkenes to 1,2-diols. The isolated Ti and Sn Lewis acid sites within the TiSn-Beta zeolite can efficiently integrate alkene epoxidation and epoxide hydration in tandem in a zeolite microreactor to achieve one-step conversion of alkenes to 1,2-diols with a high selectivity of >90%. Zeolite confinement effects result in high tandem rates of alkene epoxidation and epoxide hydration as well as high selectivity toward the desired product. Further, the novel method demonstrated herein can be employed to other tandem catalytic reactions for sustainable chemical production.

Method for catalyzing catalytic oxidation reaction of cyclopentene by vacancy silicon-tungsten heteropolyacid salt catalyst

The invention relates to a method for catalyzing a catalytic oxidation reaction of cyclopentene by utilizing a vacancy silicon-tungsten heteropolyacid salt catalyst. The invention aims to provide a process method for preparing glutaraldehyde and 1, 2-cyclopentanediol by carrying out catalytic oxidation on cyclopentene by using a two-vacancy silicon-tungsten heteropolyacid salt catalyst, which is small in environmental pollution, high in catalytic activity, high in yield and easy in recycling of the catalyst. According to the technical scheme, the method comprises the following steps of: (1) weighing cyclopentene, a heteropolyacid catalyst and 30% hydrogen peroxide according to a reaction molar ratio of 1: (0.0002-0.0020): (0.5-4.0), adding a quantitative reaction solvent, mixing well, controlling the temperature range to be 30-55 DEG C, reacting for 0.5-8 hours, and stirring until the reaction is finished; (2) carrying out a rectification process on a mixture generated by the reaction to obtain glutaraldehyde and 1, 2-cyclopentanediol; and (3) carrying out reduced pressure distillation on the reaction liquid to remove the solvent, and filtering, washing, vacuum-drying, collecting and recycling the vacancy silicon-tungsten heteropolyacid catalyst.

Understanding the mechanism of N coordination on framework Ti of Ti-BEA zeolite and its promoting effect on alkene epoxidation reaction

The function of ammonium salts on the epoxidation performance over Ti-BEA zeolite was investigated in detail. Experiments of alkene epoxidation, side reactions of epoxide and decomposition of H2O2 with or without ammonium salts were designed, and the UV-Vis spectroscopy was employed to analyze the structure of Ti-hydroperoxo species. It is revealed that the ammonia (or amines) dissociated from the ammonium salt would chelate with the linear Ti-η1(OOH) species and form a bridged Ti-η2(OOH)-R species, which is more stable, more weaker in epoxide adsorption and acidity as well. Therefore, side reactions and H2O2 decomposition would be suppressed, and both alkene conversion and epoxide selectivity would be promoted simultaneously. On the other hand, the excessive NH3?H2O (NH3/Ti>1) or NaOH bond with the Ti-η2(OOH)-R species and generate salt-like Ti-η2(OO)-M+ species, resulting in the deactivation of Ti active center. While for ammonium salts, e.g. NH4Cl, the limited dissociation degree along with the acidic environment help the Ti active center to maintain in highly active. In short, this work provides a practical Ti active center tuning method for Ti-BEA zeolite, as well as a thorough understanding of its Ti-hydroperoxo species.

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.

Catalyst Systems Based on a Metal Halide and a Quaternary Ammonium Salt in the 1,2-Epoxycyclopentane Carboxylation Reaction

Abstract: Results of a study of 1,2-epoxycyclopentane carboxylation to cyclopentene carbonate (CPC) in the presence of various catalyst systems have been described. It has been found that the reaction occurs most efficiently in the presence of cobalt (nickel) chloride (bromide) hydrate and a quaternary ammonium salt (TEAB, TBAB). It has been recommended that CPC should be synthesized under a CO2 pressure of no less than 3.5 MPa at a temperature of 140–150°С without any solvent or in the medium of a solvent, such as target CPC, DMF, or N-MP, at a 1,2-epoxycyclopentane weight fraction in the feed mixture of no less than 25%. These conditions provide the formation of CPC with a selectivity of 97–99% and almost complete epoxide conversion within 2–4 h. It has been shown that the developed catalyst system can be recycled.