2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)-

Base Information

• Chemical Name: 2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)-
• CAS No.: 53558-94-4
• Molecular Formula: C5H5 Cl O3
• Molecular Weight: 148.546
• Nikkaji Number: J429.223E
• Wikidata: Q82951082
• Mol file: 53558-94-4.mol

Synonyms:53558-94-4;2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)-;R(-)-Dihydro-2(3H)-furanone-5-carbonyl chloride;2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)- (9CI);C5H5ClO3;(R)-5-OXOTETRAHYDROFURAN-2-CARBONYL CHLORIDE;(2R)-5-oxooxolane-2-carbonyl chloride;SCHEMBL9201455;MFCD13173547;AT19708;EN300-359748;2-Furancarbonylchloride,tetrahydro-5-oxo-,(2R)-;2-Furancarbonyl chloride, tetrahydro-5-oxo-, (R)-;(R)-Tetrahydro-5-oxo-2beta-furancarboxylic acid chloride;2-Furancarbonyl chloride,tetrahydro-5-oxo-,(2R)-(9ci)

Chemical Property of 2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)-

Chemical Property:

• Vapor Pressure: 0.00256mmHg at 25°C
• Boiling Point: 286.9°Cat760mmHg
• Flash Point: 142.7°C
• PSA: 43.37000
• Density: 1.45g/cm³
• LogP: 0.45740
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.9927217
• Heavy Atom Count: 9
• Complexity: 154

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=O)OC1C(=O)Cl
• Isomeric SMILES: C1CC(=O)O[C@H]1C(=O)Cl

Technology Process of 2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)-

There total 7 articles about 2-Furancarbonyl chloride, tetrahydro-5-oxo-, (2R)- 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: 95.0%

(R)-tetrahydro-5-oxo-2-furancarboxylic acid (53558-93-3) → (R)-(-)-γ-chlorocarbonyl-γ-butyrolactone (53558-94-4)

Guidance literature:

With thionyl chloride;

DOI:10.1016/S0957-4166(00)86054-1

Reference yield: 92.0%

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (R)-(-)-γ-chlorocarbonyl-γ-butyrolactone (53558-94-4) + (S)-tetrahydro-5-oxo-2-furancarbonyl chloride (54848-33-8)

Guidance literature:

With oxalyl dichloride; In benzene; 1.) 1 h, 50 deg C; 2.) 24 h, r.t.;

DOI:10.1016/0008-6215(83)88353-0

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (R)-(-)-γ-chlorocarbonyl-γ-butyrolactone (53558-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaNO₂, aq. HCl / Ambient temperature

2: SOCl₂ / 4 h / Heating

With hydrogenchloride; thionyl chloride; sodium nitrite;

DOI:10.1016/S0957-4166(00)80249-9

upstream raw materials:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

(R)-tetrahydro-5-oxo-2-furancarboxylic acid

D-Glutamic acid

L-glutamic acid

Downstream raw materials:

(R)-tetrahydro-5-oxo-2-furancarbaldehyde

(5S,2'R,8'R,11'R,2''R,5''R,1'''S)-5-methyl-3-{2',8',11'-trihydroxy-11'-[5''-(1'''-hydroxy-pentadecyl)-tetrahydro-furan-2''-yl]-undecyl}-5H-furan-2-one

(5R,11R)-3-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-5-methoxymethoxy-11-{(R)-3-methoxymethoxy-3-[(2R,5R)-5-((S)-1-methoxymethoxy-pentadecyl)-tetrahydro-furan-2-yl]-propyl}-oxacycloundecan-2-one

4'-Octyloxy-biphenyl-4-carboxylic acid (R)-6,6-dimethyl-2-oxo-tetrahydro-pyran-3-yl ester

Refernces

• 1、 Fenneteau, Johan,Vallerotto, Sara,Ferrié, Laurent,Figadère, Bruno. "Liebeskind-Srogl cross-coupling on γ-carboxyl-γ-butyrolactone derivatives: Application to the side chain of amphidinolides C and F". supporting information. p. 3758 - 3761. Retrieved 2015/06/08.
• 2、 Levy, Stuart G.,Jacques, Vincent,Zhou, Kevin Li,Kalogeropoulos, Shirley,Schumacher, Kelly,Amedio, John C.,Scherer, Jonathan E.,Witowski, Steven R.,Lombardy, Richard,Koppetsch, Karsten. "Development of a multigram asymmetric synthesis of 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester, (R)-tert-Bu4-DOTAGA1". experimental part. p. 535 - 542. Retrieved 2010/04/22.