58920-79-9

Usage

Uses

Used in Organic Synthesis:
Methyl 1-cyanocyclobutanecarboxylate is used as an organic reagent for the synthesis of various organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, such as nucleophilic addition, substitution, and rearrangement reactions, enabling the formation of diverse organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl 1-cyanocyclobutanecarboxylate is used as a building block for the development of new drugs. Its ability to form stable intermediates and participate in complex chemical reactions makes it a valuable component in the synthesis of pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
Methyl 1-cyanocyclobutanecarboxylate is also utilized in the agrochemical industry as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its reactivity and compatibility with other chemical groups make it suitable for the development of effective and environmentally friendly agrochemical products.
Used in Material Science:
In the field of material science, methyl 1-cyanocyclobutanecarboxylate is employed as a monomer or intermediate in the synthesis of advanced polymers and materials. Its unique structure and reactivity contribute to the development of materials with specific properties, such as high strength, flexibility, or thermal stability, for various applications, including automotive, aerospace, and electronics industries.

Storage

Methyl 1-cyanocyclobutanecarboxylate should sealed in dry,2-8°C.

InChI:InChI=1/C7H9NO2/c1-10-6(9)7(5-8)3-2-4-7/h2-4H2,1H3

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 220145-21-1 1-(<<(ter-butoxy)carbonyl>amino>methyl)cyclobutane-1-carboxylic acid 

Relevant academic research and scientific papers

Ligand and metal complex

A ligand of Formula (I) is provided: wherein A4 represents a hydrogen atom, a nitro group, an amino group, a thiocyanato group, or —Z—Y, in which Z is a divalent linking group and Y is a group derived from a biocompatible molecule, with the proviso that when X is methylene, A4 cannot be a hydrogen atom or a nitro group. A metal complex having the ligand is also provided and is useful as a blood pool contrast agent or a targeting contrast agent.

Synthesis and physicochemical characterization of carbon backbone modified [Gd(TTDA)(H2O)]2- derivatives

The present study was designed to exploit optimum lipophilicity and high water-exchange rate (kex) on low molecular weight Gd(III) complexs to generate high bound relaxivity (r1b), upon binding to the lipophilic site of human serum albumin (HSA). Two new carbon backbone modified TTDA (3,6,10-tri(carboxymethyl)-3,6,10-triazadodecanedioic acid) derivatives, CB-TTDA and Bz-CB-TTDA, were synthesized. The complexes [Gd(CB-TTDA)(H 2O)]2- and [Gd(Bz-CB-TTDA)(H2O)]2- both display high stability constant (log KGdL = 20.28 and 20.09, respectively). Furthermore, CB-TTDA (log K(Gd/Zn) = 4.22) and Bz-CB-TTDA (log K(Gd/Zn) = 4.12) exhibit superior selectivity of Gd(III) against Zn(II) than those of TTDA (log K(Gd/Zn) = 2.93), EPTPA-bz-NO2 (log K(Gd/Zn) = 3.19), and DTPA (log K (Gd/Zn) = 3.76). However, the stability constant values of [Gd(CB-TTDA)(H2O)]2- and [Gd(Bz-CB-TTDA)(H 2O)]2- are lower than that of MS-325. The parameters that affect proton relaxivity have been determined in a combined variable temperature 17O NMR and NMRD study. The water exchange rates are comparable for the two complexes, 232 × 106 s-1 for [Gd(CB-TTDA)(H2O)]2- and 271 × 106 s -1 for [Gd(Bz-CB-TTDA)(H2O)]2-. They are higher than those of [Gd(TTDA)(H2O)]2- (146 × 10 6 s-1), [Gd(DTPA)(H2O)]2- (4.1 × 106 s-1), and MS-325 (6.1 × 106 s-1). Elevated stability and water exchange rate indicate that the presence of cyclobutyl on the carbon backbone imparts rigidity and steric constraint to [Gd(CB-TTDA)(H2O)]2-and [Gd(Bz-CB-TTDA) (H2O)]2-. In addition, the major objective for selecting the cyclobutyl is to tune the lipophilicity of [Gd(Bz-CB-TTDA)(H 2O)]2-. The binding affinity of [Gd(Bz-CB-TTDA)(H 2O)]2- to HSA was evaluated by ultrafiltration study across a membrane with a 30 kDa MW cutoff, and the first three stepwise binding constants were determined by fitting the data to a stoichiometric model. The binding association constants (KA) for [Gd(CB-TTDA)(H 2O)]2- and [Gd(Bz-CB-TTDA)(H2O)]2- are 1.1 × 102 and 1.5 × 103, respectively. Although the KA value for [Gd(Bz-CB-TTDA)(H2O)] 2- is lower than that of MS-325 (KA = 3.0 × 10 4), the r1b value, r1b = 66.7 mM-1 s-1 for [Gd(Bz-CB-TTDA)(H2O)] 2-, is significantly higher than that of MS-325 (r1 b = 47.0 mM-1 s-1). As measured by the Zn(II) transmetalation process, the kinetic stabilities of [Gd(CB-TTDA)(H 2O)]2-, [Gd(Bz-CB-TTDA)(H2O)]2-, and [Gd(DTPA)(H2O)]2- are similar and are significantly higher than that of [Gd(DTPA-BMA)(H2O)]2-. High thermodynamic and kinetic stability and optimized lipophilicity of [Gd(CB-TTDA)(H2O)]2- make it a favorable blood pool contrast agent for MRI.

Cycloalkyl triamine pentacarboxylate as ligands for paramagnetic metal complexes

A cycloalkyl triamine pentacarboxylate compound coordinating to a metal ion to form a high stability metal complex in serum is provided. The metal complex of the present invention can be used as a contrast agent for magnetic resonance imaging (MRI).