19456-17-8

Usage

Uses

Used in Organic Synthesis:
(4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one is used as a building block in the synthesis of complex organic molecules for its ability to undergo multiple reactions, including hydrolysis and ring-opening reactions. This versatility makes it a valuable compound in creating a wide range of organic compounds.
Used in Pharmaceutical Research:
(4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one is used as a key intermediate in the development of new pharmaceuticals due to its potential pharmacological properties. Its unique structure and reactivity contribute to the design and synthesis of novel drug candidates.
Used in Drug Development:
In the pharmaceutical industry, (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one is used as a precursor for the development of new drugs. Its potential pharmacological properties are being studied to identify its possible applications in treating various medical conditions, making it a promising compound for future drug discoveries.

Upstream product

• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 105-58-8 Diethyl carbonate 
• 79-37-8 oxalyl dichloride 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 100-52-7 benzaldehyde 
• 79-22-1 methyl chloroformate 
• 124-38-9 carbon dioxide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1439-07-2 trans-Stilbene oxide 
• 1689-71-0 2,3-diphenyloxirane 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 5773-56-8 1,2-Diphenylethanol 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 

Relevant academic research and scientific papers

NNC-Scorpionate Zirconium-Based Bicomponent Systems for the Efficient CO2Fixation into a Variety of Cyclic Carbonates

Two new derivatives of the bis(3,5-dimethylpyrazol-1-yl)methane modified by introduction of organosilyl groups on the central carbon atom, one of which bearing a chiral fragment, have been easily prepared. We verified the potential utility of these compou

Synthesis of cyclic carbonates from atmospheric pressure carbon dioxide using exceptionally active aluminium(salen) complexes as catalysts

Dimetallic aluminium(salen) complexes show exceptionally high catalytic activity for the synthesis of cyclic carbonates from terminal epoxides at ambient temperature and pressure. The process has the potential to contribute towards decreasing atmospheric

Synthesis of cyclic carbonates by ruthenium(VI) bis -imido porphyrin/TBACl-catalyzed reaction of epoxide with CO2

The catalytic activity of the ruthenium(VI) bis-imido porphyrin complex/TBACl binary system in promoting the CO2 cycloaddition to epoxides forming cyclic carbonates is here reported. The system was very efficient in catalyzing the conversion of differently substituted epoxides under mild experimental conditions (100 degC and 0.6 MPa of CO2). Even if the sole TBACl resulted active under the optimized experimental conditions, the addition of ruthenium species was fundamental to maximizing the reaction productivity both in terms of epoxide conversions and cyclic carbonate selectivities. A preliminary mechanistic study indicated a positive role of ruthenium imido nitrogen atom in activating carbon dioxide.

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: Theoretical evidence for an asynchronous concerted pathway

The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained in ratios close to 1:1 in the cyclization reactions. The best yields of these compounds were obtained in dichloromethane (DCM). Together with 16 known compounds, two novel oxazolidinone derivatives and two novel cyclic carbonates were synthesized with an efficient and straightforward method. Compared to the existing methods, the synthetic approach presented here provides the following distinct advantageous: being a one-pot reaction with metal-free reagent, having shorter reaction times, good yields and a very simple purification method. Moreover, using the density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level of theory the mechanism of the cycloaddition reactions has been elucidated. The further investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates disclosed that the cycloaddition reaction proceeds via an asynchronous concerted mechanism in gas phase and in DCM.

An Aminopyridinium Ionic Liquid: A Simple and Effective Bifunctional Organocatalyst for Carbonate Synthesis from Carbon Dioxide and Epoxides

An aminopyridinium ionic liquid is presented as a green, tunable, and active metal-free one-component catalytic system for the atom-efficient transformation of oxiranes and CO2 to cyclic carbonates. Inclusion of a positively charged moiety into aminopyridines, through a simple single-step synthesis, provides a one-component ionic liquid catalytic system with superior activity; effective in ring opening of epoxide, CO2 inclusion, and stabilization of oxoanionic intermediates. An efficiency assessment of a variety of positively charged aminopyridines was pursued, and the impact of temperature, catalyst loading, and the kind of nucleophile on the catalytic performance was also investigated. Under solvent-free conditions, this bifunctional organocatalytic system was used for the preparation of 18 examples of cyclic carbonates from a broad range of alkyl- and aryl-substituted oxiranes and CO2, where up to 98 percent yield and high selectivity were achieved. DFT calculations validated a mechanism in which nucleophilic ring-opening and CO2 inclusion occur simultaneously towards cyclic carbonate formation.

Plasma-Assisted Immobilization of a Phosphonium Salt and Its Use as a Catalyst in the Valorization of CO2

The first plasma-assisted immobilization of an organocatalyst, namely a bifunctional phosphonium salt in an amorphous hydrogenated carbon coating, is reported. This method makes the requirement for prefunctionalized supports redundant. The immobilized catalyst was characterized by solid-state 13C and 31P NMR spectroscopy, SEM, and energy-dispersive X-ray spectroscopy. The immobilized catalyst (1 mol %) was employed in the synthesis of cyclic carbonates from epoxides and CO2. Notably, the efficiency of the plasma-treated catalyst on SiO2 was higher than those of the SiO2 support impregnated with the catalyst and even the homogeneous counterpart. After optimization of the reaction conditions, 13 terminal and four internal epoxides were converted with CO2 to the respective cyclic carbonates in yields of up to 99 %. Furthermore, the possibility to recycle the immobilized catalyst was evaluated. Even though the catalyst could be reused, the yields gradually decreased from the third run. However, this is the first example of the recycling of a plasma-immobilized catalyst, which opens new possibilities in the recovery and reuse of catalysts.

Scalable, Durable, and Recyclable Metal-Free Catalysts for Highly Efficient Conversion of CO2 to Cyclic Carbonates

A series of highly active organoboron catalysts for the coupling of CO2 and epoxides with the advantages of scalable preparation, thermostability, and recyclability is reported. The metal-free catalysts show high reactivity towards a wide scope of cyclic carbonates (14 examples) and can withstand a high temperature up to 150 °C. Compared with the current metal-free catalytic systems that use mol % catalyst loading, the catalytic capacity of the catalyst described herein can be enhanced by three orders of magnitude (epoxide/cat.=200 000/1, mole ratio) in the presence of a cocatalyst. This feature greatly narrows the gap between metal-free catalysts and state-of-the-art metallic systems. An intramolecular cooperative mechanism is proposed and certified on the basis of investigations on crystal structures, structure–performance relationships, kinetic studies, and key reaction intermediates.

Synthesis of helical aluminium catalysts for cyclic carbonate formation

Helical aluminium complexes [Al2X4(μ-nbptam)] (X = Me 1, Et 2), [Al2X4(μ-fbpam)] (R = Me 3, Et 4), [Al3X7(μ-nbptam)] (X = Me 5, Et 6) and [Al3X7(μ-fbpam)] (X = Me 7, E

Influence of the Counterion on the Synthesis of Cyclic Carbonates Catalyzed by Bifunctional Aluminum Complexes

New bifunctional aluminum complexes have been prepared with the aim of studying the effect of a counterion on the synthesis of cyclic carbonates from epoxides and carbon dioxide (CO2). Neutral ligand 1 was used as a precursor to obtain four nov