2(3H)-Furanone, 3-(triphenylphosphoranylidene)-

Base Information

• Chemical Name: 2(3H)-Furanone, 3-(triphenylphosphoranylidene)-
• CAS No.: 34932-07-5
• Molecular Formula: C22H19O2P
• Molecular Weight: 346.365
• NSC Number: 100769
• UNII: 5HYJ564RMV
• DSSTox Substance ID: DTXSID50188488
• Nikkaji Number: J49.597B
• Wikidata: Q72466425
• Mol file: 34932-07-5.mol

Synonyms:34932-07-5;2(3H)-Furanone, 3-(triphenylphosphoranylidene)-;2(3H)-Furanone, dihydro-3-(triphenylphosphoranylidene)-;gamma-Butyrolactonylidene triphenyl phosphorane;NSC 100769;BRN 1260939;5HYJ564RMV;2-(Triphenylphosphoranylidene)-gamma-butyrolactone;3-(triphenyl-lambda5-phosphanylidene)oxolan-2-one;alpha-(Triphenylphosphoranylidene)-gamma-butyrolactone;NSC-100769;3-(triphenylphosphoranylidene)dihydro-2(3H)-furanone;UNII-5HYJ564RMV;Dihydro-3-(triphenylphosphoranylidene)-2(3H)-furanone;SCHEMBL3603157;C22H19O2P;DTXSID50188488;C22-H19-O2-P;MFCD00065318;NSC100769;LS-70524;.gamma.-Butyrolactonylidene triphenyl phosphorane;2-Oxotetrahydrofuran-3-ylidenetriphenylphosphorane;alpha-triphenylphosphoranylidene-gamma-butyrolactone;2-(Triphenylphosphoranylidene)-.gamma.-butyrolactone;3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one;3-(triphenylphosphoranylidene)dihydrofuran-2(3H)-one;3-(Triphenylphosphoranylidene)dihydrofuran-2-(3H)-one;.alpha.-(Triphenylphosphoranylidene)-.gamma.-butyrolactone;3-(TRIPHENYL-.LAMBDA.5-PHOSPHANYLIDENE)OXOLAN-2-ONE

Chemical Property of 2(3H)-Furanone, 3-(triphenylphosphoranylidene)-

Chemical Property:

• Vapor Pressure: 3.26E-10mmHg at 25°C
• Boiling Point: 502.1°C at 760 mmHg
• Flash Point: 270.6°C
• PSA: 36.11000
• Density: 1.23
• LogP: 3.09980
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 346.11226684
• Heavy Atom Count: 25
• Complexity: 468

Purity/Quality:

99%, ^*data from raw suppliers

2-(TRIPHENYLPHOSPHORANYLIDENE)-GAMMA-BUTYROLACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(=O)C1=P(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of 2(3H)-Furanone, 3-(triphenylphosphoranylidene)-

There total 6 articles about 2(3H)-Furanone, 3-(triphenylphosphoranylidene)- 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: 92.0%

α-bromo-γ-butyrolactone (5061-21-2) + triphenylphosphine (603-35-0) → 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone (34932-07-5)

Guidance literature:

α-bromo-γ-butyrolactone; triphenylphosphine; In tetrahydrofuran; for 15h; Reflux; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/anie.201202486

Reference yield:

triphenylphosphine (603-35-0) → 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone (34932-07-5)

Guidance literature:

triphenylphosphine; 3-halooxolan-2-one; In toluene; at 80 ℃; Inert atmosphere;

With sodium hydroxide; In dichloromethane; water; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201001379

Reference yield:

(2-oxotetrahydro-3-furanyl)triphenylphosphonium bromide (28228-78-6) → 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone (34932-07-5)

Guidance literature:

With potassium tert-butylate; In dichloromethane; for 0.5h; Yield given; Ambient temperature;

DOI:10.1021/jo00160a008

upstream raw materials:

α-bromo-γ-butyrolactone

triphenylphosphine

(2-oxotetrahydro-3-furanyl)triphenylphosphonium bromide

Downstream raw materials:

(E)-α-(2-furylmethylene)-γ-butyrolactone

(E)-N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine

E-3-(2-oxotetrahydrofuran-3-ylidine)phthalide

α-methylene-γ-butyrolactone

Refernces

• 1、 Liu, Xin,Werner, Thomas. "Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides". supporting information. p. 1096 - 1104. Retrieved 2020/12/31.
• 2、 Panchal, Heena,Clarke, Christopher,Bell, Charles,Karad, Somnath Narayan,Lewis, William,Lam, Hon Wai. "Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols". supporting information. p. 12389 - 12392. Retrieved 2018/11/20.