61699-62-5

Usage

Uses

Used in Chemical Synthesis:
3,4-Diisopropoxy-3-cyclobutene-1,2-dione is used as a synthetic intermediate for the preparation of complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-Diisopropoxy-3-cyclobutene-1,2-dione is used as a key component in the synthesis of novel drug candidates. Its ability to form diverse chemical entities makes it a promising starting material for the development of new therapeutic agents with potential applications in various medical fields.
Specific Applications:
3,4-Diisopropoxy-3-cyclobutene-1,2-dione has been specifically used in the preparation of 1,1′-bis3-(4-isopropoxy-3-cyclobutene-1,2-dioxo)ferrocene and 3-isopropoxy-4-ferrocenyl-3-cyclobutene-1,2-dione. These compounds have potential applications in various fields, such as materials science, catalysis, and medicinal chemistry, due to their unique properties and structures.

InChI:InChI=1/C10H14O4/c1-5(2)13-9-7(11)8(12)10(9)14-6(3)4/h5-6H,1-4H3

Upstream product

• 67-63-0 isopropyl alcohol 
• 2892-51-5 squaric acid 
• 4447-60-3 Triisopropoxymethan 
• 1007834-25-4 2,3-diisopropyloxy-1,3-butadiene-1,4-dione 
• 71226-39-6 poly-silver(I) squarate 

Downstream Products

• 114094-64-3 2,3-bis(1-methylethoxy)-4-hydroxy-4-phenylcyclobut-2-en-1-one 
• 114094-71-2 3-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione 
• 114094-66-5 2,3-bis(1-methylethoxy)-4-hydroxy-4-(phenylethynyl)-cyclobut-2-en-1-one 
• 1025984-34-2 2-(1-Hydroxy-2,3-diisopropoxy-4-oxo-cyclobut-2-enyl)-4-phenyl-4H-pyridine-1-carboxylic acid tert-butyl ester 
• 1027960-52-6 4-(2-Fluoro-phenyl)-2-(1-hydroxy-2,3-diisopropoxy-4-oxo-cyclobut-2-enyl)-4H-pyridine-1-carboxylic acid tert-butyl ester 
• 193540-21-5 3-Isopropoxy-4-(4-triisopropylsilanyloxy-3-triisopropylsilanyloxymethyl-phenyl)-cyclobut-3-ene-1,2-dione 

Relevant academic research and scientific papers

Mn(III)-based oxidative radical ring-expansion reaction using squarate derivatives: Selective synthesis of bis(butenolide)s and the acetate monomers

The Mn(III)-based oxidation of phenyl- and alkyl-substituted hydroxycyclobutenones selectively produced the bis(butenolide)s or the acetate monomers via the 5-endo radical cyclization depending upon the concentration of the reaction. A similar reaction of hydroxycyclobutenones bearing an alkenyl and alkynyl substituent did not produce any bis(butenolide)s or acetate monomers, but the 5-exo and 6-endo radical cyclization products including the unsaturated group. The oxidation of the hydroxycyclobutenones having an unsaturated substituent in the presence of alkenes afforded radical coupling products during the 5-exo radical cyclization. The reaction details, structure determination of the products, and the mechanism for the formation of the products are described.

Squaraine dyes containing diphenylamine group: Effects of different type structures on material properties and organic photovoltaic performances

Four donor-acceptor-donor (D-A-D’) unsymmetrical squaraines (USQs) with different molecular skeletons (XZ-type and YZ-type), containing diphenylamine group with/without methoxy substituent were synthesized as donor materials in bulk-heterojunction (BHJ) organic photovoltaics (OPVs). The introduction of methoxy group in USQs has little different effects on the overall photovoltaic performance. Conversely, the different molecular skeleton types of the USQs have significant influence on their material properties and photovoltaic performances. Compared to BIDPSQ and BIDPOMeSQ with XZ-type molecular skeleton, IDPSQ and IDPOMeSQ with YZ-type molecular skeleton display closer solid-state packing, much lower highest occupied molecular orbital (HOMO) energy level, higher hole mobility and smaller phase separation domain size. Consequently, YZ-type USQs exhibit the most excellent performance with power conversion efficiency (PCE) of ~4%, which is approximately 300% higher than those of XZ-type USQs. Surprisingly, even though IDPSQ and IDPOMeSQ show wide band gaps, the corresponding devices still achieve a highest PCE of ~4%, which is comparable to or even higher than the PCEs of some reported SQ-based devices with low band gaps. These results indicate the YZ-type molecular skeleton and the electron-donating diphenylamine group are very promising to construct highly efficient squaraine donor materials.

Protecting-Group-Free Total Synthesis and Biological Evaluation of 3-Methylkealiiquinone and Structural Analogues

The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A thermal ring expansion via 6π-conrotatory ring closure to build the quinone fragment gave rise to the desired linear analogue of the natural compound along with a nondescribed structurally attractive angular naphtho[1,2-d]imidazole regioisomer. The IC50 values for the compounds were determined on three cancer cell lines.

New syntheses and ring expansion reactions of cyclobutenimines

Two routes are reported for the synthesis of iminocyclobutenones having N-(het)aryl substitution: an addition/substitution sequence starting with cyclobutenediones and an aza-Wittig method. A new synthetic route to N-alkyl derivatives is also presented. This involves O-alkylation of 3-alkylamino-1,2-cyclobutenediones using Meerwein's reagent and subsequent deprotonation under non-hydrolytic conditions. Lithium organyls were found to add to the remaining carbonyl group. The resulting tertiary alcohols undergo ring enlargement on heating in xylene to give 4-aminophenols, 4-amino-1-naphthols, or cyclopenta-annulated quinolines from 4-vinyl, 4-aryl, and 4-alkynyl derivatives, respectively. CSIRO 2010.

Structural effects on interconversion of oxygen-substituted bisketenes and cyclobutenediones

(Graph Presented) Cyclobutenediones 5 disubstituted with HO (a), MeO (b), EtO (c), i-PrO (d), t-BuO (e), PhO (f), 4-MeOC6H4O (g), 4-O2NC6H4O (h), and 3,4-bridging OCH 2CH2O (i) substituents upon laser flash photolysis gave the corresponding bisketenes 6a-i, as detected by their distinctive doublet IR absorptions between 2075 and 2106 and 2116 and 2140 cm-1. The reactivities in ring closure back to the cyclobutenediones were greatest for the group 6b-e, with the highest rate constant of 2.95 ×107 s -1 at 25°C for 6e (RO = t-BuO) in isooctane, were less for 6a (RO = OH, k = 2.57 × 106 s-1 in CH3CN), while 6f- i were the least reactive, with the lowest rate constant of 3.8 × 104 s-1 in CH3CN for 6h (RO = 4-O 2NC6H4O). The significantly reduced rate constants for 6f-i are attributed to diminution of the electron-donating ability of oxygen to the cyclobutenediones 5f-h by the ArO substituents compared to alkoxy groups and to angle strain in the bridged product cyclobutenedione 5i. The reactivities of the ArO-substituted bisketenes 6f-h in CH3CN varied by a factor of 50 and gave an excellent correlation of the observed rate constants log k with the σp constants of the aryl substituents. Computational studies at the B3LYP/6-31G(d) level of ring-closure barriers are consistent with the measured reactivities. Photolysis of squaric acid (5a) in solution provides a convenient preparation of deltic acid (7).

An efficient general synthesis of squarate esters

An efficient and general method for the synthesis of alkyl squarates is presented. This involves the reactions of squaric acid with the desired alcohol in the presence of an orthoformate. This was applicable for the synthesis of dimethyl-, diethyl-, diisopropyl, di-n-butyl and di-t-butyl squarates in yields ranging from 77-97%. It is a convenient and safe method that can be accomplished on a multigram scale.

An Improved Method for the Synthesis of Substituted Cyclobutenediones

Practical and high yielding routes to substituted cyclobutenediones are described. 3,4-Bis(1-methylethoxy)cyclobut-3-ene-1,2-dione (diisopropyl squarate), a stable, crystalline derivative of squaric acid, was easily prepared by refluxing squaric acid in 2

Preparation of 3-Alkoxy-4-alkyl-3-cyclobutene-1,2-diones

Several squaric acid esters (2a-g) are prepared.They react with Grignard compounds to give the title compounds (11a-n). 1,2- vs. 1,4-Grignard addition and the benzyl-tolyl rearrangement coincidental with the Grignard reaction are discussed.Hydrolysis of compounds 11 leads to 4-alkyl-3-hydroxy-3-cyclobutene-1,2-diones (12).