23786-93-8

Usage

Uses

Used in Pharmaceutical Industry:
1,1-Diethoxycyclopentane is used as a reagent for the synthesis of Quinbolone (Q670150), which is a cyclopentenyl ether derivative of Boldenone (B675100) and also its active metabolite. Quinbolone exhibits weak androgenic activity, making it a potential candidate for therapeutic applications in conditions related to androgen deficiency or imbalance.
In the synthesis of Quinbolone, 1,1-diethoxycyclopentane serves as a key intermediate, contributing to the formation of the cyclopentenyl ether structure that is characteristic of this class of compounds. The weak androgenic activity of Quinbolone suggests that it may have potential applications in the treatment of conditions such as male hypogonadism, where androgen replacement therapy is indicated.
Furthermore, the use of 1,1-diethoxycyclopentane in the synthesis of Quinbolone highlights its importance in the development of novel therapeutic agents with potential applications in various medical fields. As research continues to explore the properties and potential uses of 1,1-diethoxycyclopentane, it is likely that additional applications will be discovered, further expanding the utility of 1,1-diethoxycyclopentane in the pharmaceutical industry.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 2429, 1991 DOI: 10.1016/S0040-4039(00)74345-0

InChI:InChI=1/C9H18O2/c1-3-10-9(11-4-2)7-5-6-8-9/h3-8H2,1-2H3

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 120-92-3 cyclopentanone 
• 64-17-5 ethanol 
• 142-29-0 cyclopentene 

Downstream Products

• 90642-20-9 2-dimethylamino-cyclopent-1-enecarbaldehyde 
• 62041-55-8 2-((dimethylamino)methylene)cyclopentanone 
• 10444-38-9 ethyl 4-cyanobutyrate 
• 108276-26-2 N-(8-Methyl-7-oxo-6,10-dioxa-spiro[4.5]dec-8-yl)-benzamide 
• 131087-26-8 (2S,3S,4R)-3-Benzyloxy-1,2-cyclopentylidenedioxy-4-hydroxyheptane 
• 931-20-4 1-methylpiperidin-2-one 
• 131087-27-9 (2S,3R,4R)-1,2-Cyclopentylidendioxy-3,4-dibenzyloxyheptane 
• 120-92-3 cyclopentanone 
• 2487-63-0 Quinbolone 
• 38553-32-1 (8R,9S,10R,13S,14S,17S)-17-(Cyclopent-1-enyloxy)-4-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 3000-64-4 Oestradiol-3-benzoat-17- 
• 28791-87-9 1,1-di(pyrazol-1-yl)cyclopentane 
• 42019-88-5 (2E,5E)-2,5-bis(4-chlorobenzylidene)cyclopentanone 
• 5447-53-0 (2E,5E)-2,5-bis(4-methoxybenzylidene)cyclopentanone 

Relevant academic research and scientific papers

2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a highly efficient and mild catalyst for diethyl acetalization of carbonyl compounds

Various types of structurally different carbonyl compounds in the presence of ethyl orthoformate (EtO)3CH could be efficiently converted to their diethyl acetals by using a catalytic amount (1-3 mol%) of DDQ under mild reaction conditions.

A facile procedure for acetalization of aldehydes and ketones catalyzed by cerium(III) trifluoromethanesulfonate

Aldehydes and ketones are readily protected in the presence of trialkyl orthoformate and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild conditions to give the corresponding acetals in good to excellent yields. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates. Copyright

Highly regioselective synthesis of trifluoromethyl derivatives of pyrazolo[1,5-a]pyrimidines bearing fused cycloalkane rings using (2-ethoxycycloalkenyl)-2,2,2-trifluoroethanones

8-Trifluoromethyl-6,7-dihydro-5H-1,4,8a-triaza-s-indacene and 9-trifluoromethyl-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazolines were efficiently generated by condensation of 5(3)-aminopyrazoles with (2-ethoxycycloalkenyl)-2,2,2-trifluoroethanones and isolated in excellent yields. The regiochemistry of the prepared compounds was established by 1H, 13C and 19F NMR spectroscopy and X-ray diffraction analysis.

One-pot synthesis of functionalized 3-(trifluoromethyl)phenols by [3+3] cyclization of 1,3-bis(silyl enol ethers) with α,β-unsaturated trifluoromethyl ketones

Functionalized 3-(trifluoromethyl)phenols were prepared by formal [3+3] cyclization of 1,3-bis(silyl enol ethers) with readily available open-chained and cyclic α,β-unsaturated trifluoromethyl ketones. The reaction of 3,4-dihydro-5-(trifluoroacetyl)-2H-pyran with 1,3-bis(silyl enol ethers) resulted in a domino process to give new functionalized dihydropyrans. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Bronsted acidic ionic liquids as efficient and recyclable catalysts for protection of carbonyls to acetals and ketals under mild conditions

A series of acidic ionic liquids have been used as efficient catalysts for the protection of various carbonyl compounds at room temperature. The features of mild conditions, satisfactory isolated yield, simple workup, and the recyclability of the catalyst were present in this process. Copyright Taylor & Francis, Inc.

Sulfamic acid as a cost-effective and recyclable catalyst for protection of carbonyls to acetals and ketals under mild conditions

An efficient H2NSO3H-catalyzed protection of various carbonyl compounds at room temperature was investigated. The features of mild conditions, cost-efficient catalyst, simple workup, and the recyclability of the catalyst were represented in this process.

A highly efficient and chemoselective method for acetalization of carbonyl compounds catalyzed by TiO2/SO42- solid superacid

Various types of aldehydes and ketones could be converted to their corresponding diethyl acetals with triethylorthoformate in the presence of TiO2/SO42- solid superacid in good to excellent yield under mild reaction conditions.

2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO) as a versatile, efficient, and chemoselective catalyst for the acetalization and transacetalization of carbonyl compounds, the preparation of acetonides from epoxides and acylals (1,1-diacetates) from aldehydes

The efficient and chemoselective preparation of acetals and ketals from carbonyl compounds, transacetalization reactions, the conversion of epoxides to acetonides, and the preparation of acylals from aldehydes in the presence of catalytic amounts of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) are described.

New routes to diethyl 1-alkenylphosphoramidates

New routes to N-(diethoxyphosphoryl)imines derived from enolizable carbonyl compounds have been investigated. Three different procedures were studied: (i) the aza-Claisen condensation of ethyl-[N-(diethoxyphosphoryl)]-formimidate with enolizable ketones, (ii) the reaction between diethyl N-sulfinylphosphoramidate and aliphatic aldehydes, and (iii) the thermally induced reaction of diethyl phosphoramidate with ketone diethyl acetals. With two exceptions in all cases the products were identified as diethyl 1-alkenylphosphoramidates with no spectroscopically detectable amounts of imine tautomers. The aza-Claisen condensation can be recommended as a simple and effective route to diethyl 1-alkenyl-3-oxophosphoramidates. (C) 2000 Elsevier Science Ltd.

Cadmium iodide catalyzed and efficient synthesis of acetals under microwave irradiations

A new selective method of acetalization of aldehydes and ketones with 1,2-diols, 1,3-diols or alcohols mediated by cadmium iodide under microwave irradiation is achieved in excellent yields.