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 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 1439-07-2 trans-Stilbene oxide 
• 124-38-9 carbon dioxide 
• 1689-71-0 2,3-diphenyloxirane 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 109-65-9 1-bromo-butane 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 100-52-7 benzaldehyde 
• 79-22-1 methyl chloroformate 
• 530-62-1 1,1'-carbonyldiimidazole 

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.

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.

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.