2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro-

Base Information

• Chemical Name: 2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro-
• CAS No.: 34638-26-1
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.155
• DSSTox Substance ID: DTXSID50480217
• Mol file: 34638-26-1.mol

Synonyms:34638-26-1;2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro-;SCHEMBL7959049;DTXSID50480217

Chemical Property of 2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro-

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 142

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C=CC2C1OC(C2)O

Technology Process of 2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro-

There total 2 articles about 2H-Cyclopenta[b]furan-2-ol, 3,3a,6,6a-tetrahydro- 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: 100.0%

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → 2-Oxabicyclo[3,3,0]oct-6-en-3-ol (34638-26-1,107244-10-0,107244-11-1)

Guidance literature:

With diisobutylaluminium hydride; In toluene;

DOI:10.1016/S0040-4020(01)81718-X

Reference yield: 98.0%

cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (+/-)-cis-2-Oxabicyclo<3.3.0>oct-6-en-3ξ-ol (34638-26-1,107244-10-0,107244-11-1)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; pentane; at -78 ℃; for 4h;

DOI:10.1039/P19950003067

Reference yield:

(+/-)-cis-2-Oxabicyclo<3.3.0>oct-6-en-3ξ-ol (34638-26-1,107244-10-0,107244-11-1) → (2S*,2aR*,4aS*,5R*,6aS*,6bR*)-Octahydro-5-(tert-butyldiphenylsiloxy)-2-methylcyclopentapentalen-1(2H)-one

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) EtMgBr / 1.) THF, 15 min, 2.) THF, room temp., 12 h

3: 95 percent / H₂ / 10percent Pd/C / ethyl acetate / 8 h / 760 Torr

4: 73 percent / K₂CO₃ / methanol

With ethylmagnesium bromide; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1021/jo00126a049

upstream raw materials:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

cis-(±)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

C₂₃H₂₄O₂

C₂₄H₂₆O₃

(4aS,5R,6aS,6bR)-3,5-Bis-benzyloxy-4,4a,5,6,6a,6b-hexahydro-3H-cyclopenta[cd]pentalen-1-one

C₂₄H₂₂Cl₂O₅

Refernces

• 1、 Broom, Nigel,O'Hanlon, Peter J.,Simpson, Thomas J.,Stephen, Rosamund,Willis, Christine L.. "Studies on the stereoselectivity of osmylation of cis-bicyclooct-6-enes". . p. 3067 - 3072. Retrieved 2007/10/03.
• 2、 Theil, Fritz,Costisella, Burkhard,Gross, Hans,Schick, Hans,Schwarz, Sigfrid. "A Three-step Procedure for the Conversion of γ-Lactones into δ-Lactones". . p. 2469 - 2472. Retrieved 2007/10/02.