694-47-3

Usage

Uses

Used in Organic Synthesis:
(1R,3S)-Cyclopent-4-ene-1,3-diol is utilized as a key intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure, which includes a double bond and two alcohol groups, allows for versatile chemical reactions and the formation of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1R,3S)-Cyclopent-4-ene-1,3-diol is employed as a building block for the development of novel drugs. Its chiral nature and specific atomic arrangement make it a valuable component in the synthesis of enantiomerically pure pharmaceutical agents, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Biotechnology Industry:
(1R,3S)-Cyclopent-4-ene-1,3-diol may also find applications in the biotechnology sector, where its unique structure and properties could be harnessed for the design of bioactive molecules. These molecules could have potential uses in therapeutics, diagnostics, or as research tools for studying biological processes.

Upstream product

• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 98-00-0 (2-furyl)methyl alcohol 
• 542-92-7 cyclopenta-1,3-diene 
• 7129-41-1 6-oxabicyclo[3.1.0]hex-2-ene 

Downstream Products

• 94258-98-7 (+/-)-trans-1.3-bis-(4-nitro-benzoyloxy)-cyclopentane 
• 94375-08-3 (+/-)-trans-3.5-bis-(3.5-dinitro-benzoyloxy)-cyclopentene-⁽¹⁾ 

Relevant academic research and scientific papers

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

Chemoenzymatic routes to cyclopentenols: The role of protecting groups on stereo- and enantioselectivity

Enantiopure (R)-4-triisopropylsilyloxycyclopent-2-en-1-one was obtained through short sequences including either the enzymatic resolution of racemic cis-4-triisopropylsilyloxycyclopent-2-en-1-ol or the enzymatic desymmetrization of cis-cyclopent-2-en-1,3-diol. Alternatively, the enantiopure (S)-4-triisopropylsilyloxycyclopent-2-en-1-one was very efficiently obtained from diacetate of cis-cyclopent-2-en-1,3-diol using enzymatic desymmetrization with CAL-B. In these sequences, TIPS proved to be the best protecting group.

A regioselective synthesis of 4-methyl-1-pyrindan-5-one

The enamine 7 reacts with crotonic aldehyde in the presence of p-toluenesulphonic acid via the intermediate 8 to yield regioselectively the unknown title compound 9. In alkaline medium, 9 is also formed from 7 and acetylacetaldehyde dimethyl acetal as well as small amounts of 11 and 12; under acidic conditions, however, mixtures of the regioisomers 9/9a are obtained in poor yield. 9a can be separated by fractional crystallisation of the hydrochlorides. Corresponding to 7 the homologous enamine 13 and acetylacetaldehyde acetal by alkaline catalysis gives the 4-methyltetrahydroquinolinone 1, respectively. Improved experimental details for an efficient preparation of the starting compounds 3 and 4 are given.

Vinyl Epoxide Hydrolysis Reactions

The rates of hydrolysis of cyclopentadiene oxide (3), cyclohexadiene oxide (4), cycloheptadiene oxide (5), cyclooctadiene oxide (6), butadiene oxide (7), and styrene oxide (8) have been determined as a function of pH.Each epoxide exhibited acid-catalyzed hydrolysis at low pH, and 3-5 showed significant rates for "spontaneous" reaction with solvent at intermediate pH values.The hydrolyses of several of the vinyl epoxides (4 and 5) showed kinetic terms in HO- at pH > ca. 13.Specific chloride effects attributed to nucleophilic addition of Cl- to neutral epoxide were observed for those compounds (3, 4, and 8) hydrolyzed in KCl solutions.From kinetic and product studies, mechanisms for hydrolyses of the vinyl epoxides are postulated.Acid-catalyzed hydrolyses of 3, 4, 5, and 6 were found to be A-1 in nature, proceeding via intermediate allyl cations.Product distributions depended on the structure of the cation.Mechanisms and product distributions for the spontaneous hydrolyses of vinyl epoxides were found to be variable, and dependent on the structure of the epoxide.