(3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one
• CAS No.: 67999-51-3
• Molecular Formula: C₈H₉IO₂
• Molecular Weight: 264.063
• Mol file: 67999-51-3.mol

Synonyms:(3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Chemical Property of (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

There total 3 articles about (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-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: 77.0%

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one (67999-51-3)

Guidance literature:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid; With iodine; sodium carbonate; potassium iodide; In water; for 0.5h;

With sodium thiosulfate; In dichloromethane; water;

Reference yield: 70.0%

Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1S,5S,6S)-6-benzoyloxy-spiro[4.4]non-1-yl ester → (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one (67999-51-3) + (1S,2R,4R,5R,6R)-5-Iodbicyclo<2.2.1>heptan-2,6-carbolacton (67999-52-4) + Benzoic acid (1R,5R,6R)-6-acryloyloxy-spiro[4.4]non-1-yl ester (186269-11-4)

Guidance literature:

With iodine; sodium hydrogencarbonate; potassium iodide; In dichloromethane; Yield given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(96)00459-4

Reference yield:

(-)-menthyl acrylate (4835-96-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one (67999-51-3) + (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7)

Guidance literature:

Multistep reaction;

DOI:10.1023/A:1012374828303

upstream raw materials:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(-)-menthyl acrylate

cyclopenta-1,3-diene

Downstream raw materials:

endo-norbornenecarboxylic acid

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid