Hexahydrofuro[2,3-b]furan

Base Information

• Chemical Name: Hexahydrofuro[2,3-b]furan
• CAS No.: 26457-63-6
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.144
• DSSTox Substance ID: DTXSID60949340
• Nikkaji Number: J1.704.510E
• Wikidata: Q82927240
• Mol file: 26457-63-6.mol

Synonyms:hexahydrofuro[2,3-b]furan;26457-63-6;perhydrofuro[2,3-b]furan;Furo(2,3-b)furan, hexahydro-;2,8-Dioxabicyclo(3.3.0)octane;perhydrofuro[2,3b]furan;tetrahydrofuro[2,3-b]furan;SCHEMBL123556;SCHEMBL179699;SCHEMBL309845;SCHEMBL8227125;SCHEMBL15849491;DTXSID60949340;IHKOXYNAMXNNDK-UHFFFAOYSA-N

Chemical Property of Hexahydrofuro[2,3-b]furan

Chemical Property:

• PSA: 18.46000
• LogP: 0.76930
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 82.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2C1CCO2

Technology Process of Hexahydrofuro[2,3-b]furan

There total 12 articles about Hexahydrofuro[2,3-b]furan 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: 72.0%

(E)-pent-2-ene-1,5-diol (25073-26-1) + carbon monoxide (201230-82-2) → tetrahydro-2H-2-pyranol (694-54-2) + 2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan (123703-40-2,26457-63-6)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine; In dichloromethane; at 120 ℃; for 20h; under 45003.6 Torr;

DOI:10.1021/ol017083o

Reference yield: 72.0%

(E)-pent-2-ene-1,5-diol (25073-26-1) + carbon monoxide (201230-82-2) → tetrahydro-2H-2-pyranol (694-54-2) + 1 ,5-pentanediol (111-29-5) + 2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan (123703-40-2,26457-63-6) + 3-hydroxymethyltetrahydropyran-2-ol

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine; In dichloromethane; at 120 ℃; for 20h; under 45003.6 Torr; Further Variations:; Reagents; Solvents; Product distribution;

DOI:10.1021/ol017083o

Reference yield: 72.0%

pent-2-ene-1,5-diol (29293-07-0) + carbon monoxide (201230-82-2) → 2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan (123703-40-2,26457-63-6)

Guidance literature:

With hydrogen; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In dichloromethane; at 120 ℃; for 20h; under 45004.5 Torr;

DOI:10.1021/ol017083o

upstream raw materials:

4-[(tert-butyldimethylsilyl)oxy]-2-{2-[(tert-butyldimethylsilyl)oxy]ethyl}butanal

(E)-pent-2-ene-1,5-diol

carbon monoxide

pent-2-ene-1,5-diol

Refernces

• 1、 Roggenbuck, Rafael,Schmidt, Andreas,Eilbracht, Peter. "Synthesis of Furo[2,3b]furans and Furo[2,36]pyrans via rhodium-catalyzed tandem hydroformylation/acetalization". . p. 289 - 291. Retrieved 2007/10/03.
• 2、 Vader,Sengers,De Groot. "The stereoselective syntheses of substituted furo[2,3b]furans". . p. 2131 - 2142. Retrieved 2007/10/02.