(3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Base Information

• Chemical Name: (3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
• CAS No.: 16822-06-3
• Molecular Formula: C9H12 O2
• Molecular Weight: 152.193
• European Community (EC) Number: 240-843-3
• Nikkaji Number: J313.892E
• Mol file: 16822-06-3.mol

Synonyms:16822-06-3;(3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one;SCHEMBL24299728;JZULHXPIDKRFAY-YUMQZZPRSA-N;3-Methylene-3abeta,4,5,6,7,7abeta-hexahydrobenzofuran-2(3H)-one

Chemical Property of (3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Chemical Property:

• Vapor Pressure: 0.00199mmHg at 25°C
• Boiling Point: 291.1°C at 760 mmHg
• Flash Point: 117.8°C
• PSA: 26.30000
• Density: 1.08g/cm³
• LogP: 1.65820
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C2CCCCC2OC1=O
• Isomeric SMILES: C=C1[C@@H]2CCCC[C@@H]2OC1=O

Technology Process of (3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

There total 160 articles about (3As,7aS)-3-methylidene-3a,4,5,6,7,7a-hexahydro-1-benzofuran-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: 98.0%

methyl trans-octahydro-3-bromomethyl-2-oxo-3-benzofurancarboxylate → trans-3-methylenehexahydrobenzofuran-2-one (3727-53-5,16822-06-3,38602-11-8,53387-38-5,61248-47-3,78684-19-2,134309-30-1)

Guidance literature:

With aluminum oxide; at 160 - 230 ℃; under 0.5 - 1 Torr;

Reference yield: 95.0%

trans-2-(α-bromovinyl)cyclohexanol (76334-37-7,78631-34-2,67964-37-8,76334-38-8,78631-33-1) → trans-3-methylenehexahydrobenzofuran-2-one (3727-53-5,16822-06-3,38602-11-8,53387-38-5,61248-47-3,78684-19-2,134309-30-1)

Guidance literature:

With triethylamine; In benzene; at 65 ℃; for 0.2h;

DOI:10.1021/jo00321a040

Reference yield: 94.0%

2-((1S,2R)-2-Hydroxy-cyclohexyl)-acrylic acid ethyl ester (54815-42-8,111211-94-0) → trans-3-methylenehexahydrobenzofuran-2-one (3727-53-5,16822-06-3,38602-11-8,53387-38-5,61248-47-3,78684-19-2,134309-30-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 60 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)95805-2

upstream raw materials:

carbon monoxide

trans-2-(α-bromovinyl)cyclohexanol

trans-2-ethynylcyclohexan-1-ol

2-((1R,2S)-2-Hydroxy-cyclohexyl)-acrylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Downstream raw materials:

4,4-bis(ethylthio)-6-(trans-2-hydroxycyclohexyl)-1,3-cylohexanedione

4,4-bis(ethylthio)-6-(trans-2-hydroxycyclohexyl)-1,3-cylohexanedione (enol form)

4,4-bis(ethylthio)-6-(cis-2-hydroxycyclohexyl)-1,3-cylohexanedione (enol form)

4,4-bis(ethylthio)-6-(cis-2-hydroxycyclohexyl)-1,3-cylohexanedione