4beta-Phenyl-1,3-dioxolane-2-one

Base Information

• Chemical Name: 4beta-Phenyl-1,3-dioxolane-2-one
• CAS No.: 90970-80-2
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.161
• DSSTox Substance ID: DTXSID00435232
• Nikkaji Number: J1.625.361H
• Wikidata: Q82250020
• Mol file: 90970-80-2.mol

Synonyms:CTK3I1385;4beta-Phenyl-1,3-dioxolane-2-one;90970-80-2;DTXSID00435232

Chemical Property of 4beta-Phenyl-1,3-dioxolane-2-one

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(=O)O1)C2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](OC(=O)O1)C2=CC=CC=C2

Technology Process of 4beta-Phenyl-1,3-dioxolane-2-one

There total 19 articles about 4beta-Phenyl-1,3-dioxolane-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

carbon dioxide (124-38-9,18923-20-1) + (S)-styrene oxide (20780-54-5) → (4S)-4-phenyl[1,3]dioxolan-2-one (4427-92-3,90971-11-2,129097-94-5,90970-80-2)

Guidance literature:

With tetrabutylammomium bromide; In acetonitrile; at 50 ℃; for 6h; optical yield given as %ee; Electrochemical reaction;

DOI:10.1039/c1cc15467b

Reference yield: 93.0%

(S)-1-phenyl-1,2-ethanediol (25779-13-9) + trichloromethyl chloroformate (503-38-8) → (4S)-4-phenyl[1,3]dioxolan-2-one (4427-92-3,90971-11-2,129097-94-5,90970-80-2)

Guidance literature:

With pyrographite; In tetrahydrofuran; at 50 ℃; for 48h;

DOI:10.1055/s-2006-926340

Reference yield: 90.0%

carbon dioxide (124-38-9,18923-20-1) + (S)-1-phenyl-1,2-ethanediol (25779-13-9) → (4S)-4-phenyl[1,3]dioxolan-2-one (4427-92-3,90971-11-2,129097-94-5,90970-80-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 70 ℃; for 18h; under 7500.75 Torr; Autoclave;

DOI:10.1002/ejoc.201400031

upstream raw materials:

4-Phenyl-1,3-dioxolan-2-one

(S)-1-phenyl-1,2-ethanediol

carbonic acid dimethyl ester

methyl-malonic acid dimethylester

Downstream raw materials:

(S)-2-Amino-1-phenyl-1-ethanol

D-2-phenylglycinol

(S)-2-azido-1-phenylethanol

(R)-2-azido-2-phenylethan-1-ol

Refernces

• 1、 Emelyanov, Mikhail A.,Stoletova, Nadezhda V.,Smol'Yakov, Alexander F.,Il'In, Mikhail M.,Maleev, Victor I.,Larionov, Vladimir A.. "Synthesis and a Catalytic Study of Diastereomeric Cationic Chiral-at-Cobalt Complexes Based on (R, R)-1,2-Diphenylethylenediamine". . p. 13960 - 13967. Retrieved 2021/09/11.
• 2、 Hu, Yuya,Wei, Zhihong,Frey, Anna,Kubis, Christoph,Ren, Chang-Yue,Spannenberg, Anke,Jiao, Haijun,Werner, Thomas. "Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts". . p. 363 - 372. Retrieved 2020/11/30.