144913-06-4

Basic information

• Product Name: 3-(BENZYLAMINO)-4-ETHOXYCYCLOBUT-3-ENE-1,2-DIONE
• Synonyms: 3-(BENZYLAMINO)-4-ETHOXYCYCLOBUT-3-ENE-1,2-DIONE;3-BENZYLAMINO-4-ETHOXYCYCLOBUT-3-EN-1,2-DIONE
• CAS NO: 144913-06-4
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 144913-06-4.mol

Chemical Properties

• Melting Point: 68℃
• Boiling Point: 396°C at 760 mmHg
• Flash Point: 193.3°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 3-(BENZYLAMINO)-4-ETHOXYCYCLOBUT-3-ENE-1,2-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(BENZYLAMINO)-4-ETHOXYCYCLOBUT-3-ENE-1,2-DIONE(144913-06-4)
• EPA Substance Registry System: 3-(BENZYLAMINO)-4-ETHOXYCYCLOBUT-3-ENE-1,2-DIONE(144913-06-4)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 144913-06-4(Hazardous Substances Data)

Usage

General Description

3-(Benzylamino)-4-ethoxycyclobut-3-ene-1,2-dione is a chemical compound that contains a cyclic structure with a four-membered ring and a carbonyl group, indicating its potential reactivity and function as a ketone. Additionally, it contains an amino group attached to a benzyl substituent, as well as an ethoxy group, indicating its potential use in organic synthesis and pharmaceutical applications. The compound's unique structure and reactive functional groups make it an interesting target for chemical and pharmaceutical research, with potential applications in drug development and organic chemistry.

InChI:InChI=1/C13H13NO3/c1-2-17-13-10(11(15)12(13)16)14-8-9-6-4-3-5-7-9/h3-7,14H,2,8H2,1H3

Upstream product

• 5231-87-8 3,4-diethoxy-3-cyclobuten-1,2-dione 
• 100-46-9 benzylamine 

Downstream Products

• 1228363-01-6 3-(benzylamino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione 
• 1253115-31-9 3-(benzylamino)-4-(((1R)-(6-methoxyquinolin-4-yl)((2S,4S,5S)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione 
• 1541171-04-3 3-(benzylamino)-4-((1-benzylpiperidin-4-yl)amino)cyclobut-3-ene-1,2-dione 
• 1025807-09-3 [(2-Amino-3,4-dioxo-cyclobut-1-enyl)-benzyl-amino]-acetic acid tert-butyl ester 
• 1027904-37-5 [Benzyl-(2-ethoxy-3,4-dioxo-cyclobut-1-enyl)-amino]-acetic acid tert-butyl ester 

Relevant articles and documents

Chiral aminoalcohols and squaric acid amides as ligands for asymmetric borane reduction of ketones: Insight to in situ formed catalytic system by DOSY and multinuclear NMR experiments

A series of squaric acid amides (synthesized in 66–99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH3?SMe2. In all cases, the aminoalcohols demonstrated better efficiency (up to 94% ee), while only poor asymmetric induction was achieved with the corresponding squaramides. A mechanistic insight on the in situ formation and stability at room temperature of intermediates generated from ligands and borane as possible precursors of the oxazaborolidine-based catalytic system has been obtained by1H DOSY and multinuclear 1D and 2D (1H,10/11B,13C,15N) NMR spectroscopy of equimolar mixtures of borane and selected ligands. These results contribute to better understanding the complexity of the processes occurring in the reaction mixture prior to the possible oxazaborolidine formation, which play a crucial role on the degree of enantioselectivity achieved in the borane reduction of α-chloroacetophenone.

Adenosine analogs bearing phosphate isosteres as human MDO1 ligands

The human O-acetyl-ADP-ribose deacetylase MDO1 is a mono-ADP-ribosylhydrolase involved in the reversal of post-translational modifications. Until now MDO1 has been poorly characterized, partly since no ligand is known besides adenosine nucleotides. Here, we synthesized thirteen compounds retaining the adenosine moiety and bearing bioisosteric replacements of the phosphate at the ribose 5′-oxygen. These compounds are composed of either a squaryldiamide or an amide group as the bioisosteric replacement and/or as a linker. To these groups a variety of substituents were attached such as phenyl, benzyl, pyridyl, carboxyl, hydroxy and tetrazolyl. Biochemical evaluation showed that two compounds, one from both series, inhibited ADP-ribosyl hydrolysis mediated by MDO1 in high concentrations.

Modularly evolved 2-aminodmap/squaramides as highly active bifunctional organocatalysts in Michael addition

We report a new family of chiral bifunctional acid/base type organocatalysts, 2-aminoDMAP/Squaramides, which are proved to be highly active (1 mol % cat. loading) promoters in conjugate addition of dibenzoylmethane to various trans-β-nitroalkenes. Steric demand of the catalysts was clearly seen by a set-by-set modulation of the squaramide unit through electronic and steric factors. The synergistic cooperation of 2-aminoDMAP "uperbase" and sterically encumbered squaramide (H-bond donor) enabled complete conversion of a range of reactants into corresponding Michael adducts in a couple of hours with exquisite selectivities (up to 98% ee).

Synthesis and biological evaluation of N, N ′-squaramides with high in vivo efficacy and low toxicity: Toward a low-cost drug against Chagas disease

Access to basic drugs is a major issue in developing countries. Chagas disease caused by Trypanosoma cruzi is a paradigmatic example of a chronic disease without an effective treatment. Current treatments based on benznidazole and nifurtimox are expensive, ineffective, and toxic. N,N′-Squaramides are amide-type compounds that feature both hydrogen bond donor and acceptor groups and are capable of multiple interactions with complementary sites. When combined with amine and carboxylic groups, squaramide compounds have increased solubility and therefore make suitable therapeutic agents. In this work, we introduce a group of Lipinski's rule of five compliant squaramides as candidates for treating Chagas disease. The in vivo studies confirmed the positive expectations arising from the preliminary in vitro studies, revealing compound 17 to be the most effective for both acute and chronic phases. The activity, stability, low cost of starting materials, and straightforward synthesis make amino squaramides appropriate molecules for the development of an affordable anti-Chagasic agent.

Tether-free immobilized bifunctional squaramide organocatalysts for batch and flow reactions

This paper describes the preparation of highly efficient, easily accessible, and robust immobilized bifunctional organocatalysts. There was no need to employ any tether to secure high enantio- and diastereoselectivities in various Michael addition reactions. The synthetically useful Michael adducts were obtained within reasonable reaction times with the advantage of easy product isolation and the possibility of automation by using a flow chemistry apparatus. Easily accessible, robust, and cheap immobilized organocatalysts are developed and used to prepare Michael adducts in excellent yields with excellent enantioselectivities, even on the gram scale. Copyright

Rationally designed squaryldiamides - A novel class of sugar-nucleotide mimics?

Sugar-nucleotides such as GDP-mannose, GDP-fucose and UDP-glucose are important biomolecules with a central role in carbohydrate and glycoconjugate biosynthesis, metabolism and cell signalling. Analogues and mimics of naturally occurring sugar-nucleotides are sought after as chemical tools and inhibitor candidates for sugar-nucleotide-dependent enzymes including glycosyltransferases. Many sugar-nucleotides bind to their target glycosyltransferases via coordination of the diphosphate group to a divalent metal cofactor in the active site. The identification of uncharged, chemically stable surrogates for the diphosphate group, with the ability to coordinate to a divalent metal, is therefore an important design criteria for the development of sugar-nucleotide mimics. Here, we describe the rational design and synthesis of a novel class of sugar-nucleotide mimics based on a squaryldiamide scaffold, an uncharged phosphate isostere. We demonstrate by comprehensive NMR titration experiments that the new sugar-nucleotide mimics coordinate efficiently to Mg2+, and provide results from biological studies with a therapeutically relevant mannosyltransferase from Trypanosoma brucei. Our findings suggest that squaryldiamides are a promising template for the development of sugar-nucleotide mimics, and illustrate the considerable potential of the squarylamide group as a fragment for inhibitor design. The Royal Society of Chemistry 2010.

Bioisosteric replacement of the α-amino carboxylic acid functionality in 2-amino-5-phosphonopentanoic acid yields unique 3,4-diamino-3-cyclobutene- 1,2-dione containing NMDA antagonists

In this report, a novel bioisostere of the α-amino acid, 3,4-diamino-3- cyclobutene-1,2-dione, has been incorporated into a series of compounds which are NMDA antagonists. These compounds, which are achiral and easily prepared, demonstrated good affinity at the NMDA receptor by their ability to displace [3H]CPP binding in vitro. In particular, the phosphonic acid 24 provided protection against NMDA-induced lethality in mice equivalent to 2-amino-7- phosphonoheptanoic acid (5). This was considered an encouraging result in lieu of the fact that 24, like 5, lacks the conformational rigidity of the more potent NMDA antagonists. In addition, analogs that incorporate the 1,2,4-oxadiazolidine-3,5-dione heterocycle of quisqualic acid and the unsaturation of kainic acid were prepared to explore selectivity at the non- NMDA receptor subtypes.