19456-17-8

Basic information

• Product Name: (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one
• Synonyms: (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one;(4S,5R)-4β,5β-Diphenyl-1,3-dioxolane-2-one
• CAS NO: 19456-17-8
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Mol File: 19456-17-8.mol
• Article Data: 39

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one(19456-17-8)
• EPA Substance Registry System: (4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one(19456-17-8)

Safety Data

• Hazardous Substances Data: 19456-17-8(Hazardous Substances Data)

Usage

Description

(4S,5R)-4,5-Diphenyl-1,3-dioxolane-2-one, with the molecular formula C16H12O3, is a white crystalline solid that serves as a crucial component in organic synthesis and pharmaceutical research. As a cyclic acetal, it features a functional group with a carbon atom bonded to two -OR groups, allowing it to participate in various chemical reactions, such as hydrolysis and ring-opening reactions. Its potential pharmacological properties also make it a subject of interest for drug development.

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 
• 645-49-8 cis-stilben 
• 201230-82-2 carbon monoxide 
• 109-65-9 1-bromo-butane 
• 102-09-0 bis(phenyl) carbonate 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 

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 articles and documents

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 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.

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.

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.