(3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione

Base Information

• Chemical Name: (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione
• CAS No.: 89026-40-4
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• UNII: 9GAP3C3DDW
• DSSTox Substance ID: DTXSID801125340
• Nikkaji Number: J156.737C
• Wikidata: Q105165198
• Mol file: 89026-40-4.mol

Synonyms:(+)-Umbellifolide;(3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione;89026-40-4;Umbellifolide, (+)-;9GAP3C3DDW;SCHEMBL21807699;CHEBI:181193;DTXSID801125340;(3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzofuran-2,5-dione;(3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzouran-2,5-dione;(3AS,6S,7AS)-6-METHYL-3-METHYLIDENE-6-(4-OXIDANYLIDENEPENTYL)-3A,4,7,7A-TETRAHYDRO-1-BENZOFURAN-2,5-DIONE;2,5(3H,4H)-Benzofurandione, tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-, (3aR,6R,7aR)-;2,5(3H,4H)-Benzofurandione, tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-, [3aR-(3aalpha,6alpha,7aalpha)]-;NCGC00384721-01!(3aR,6R,7aR)-6-methyl-3-methylidene-6-(4-oxopentyl)-3a,4,7,7a-tetrahydro-1-benzofuran-2,5-dione

Chemical Property of (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione

Chemical Property:

• PSA: 60.44000
• LogP: 2.21270
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCCC1(CC2C(CC1=O)C(=C)C(=O)O2)C
• Isomeric SMILES: CC(=O)CCC[C@@]1(C[C@@H]2[C@H](CC1=O)C(=C)C(=O)O2)C

Technology Process of (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione

There total 4 articles about (3aR,6R,7aR)-Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione 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:

11β-phenylseleno-7α,8βH-eudesm-4-en-12,8-olide (113018-56-7) → umbellifolide (89026-40-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) 1M aqueous NaOH, 2) 5percent aqueous AcOH / 1) EtOH, reflux, 1h, 2) 0 deg C, ether

2: 89 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / 0 °C

3: 1) 1M aqueous NaOH, / 1) EtOH, reflux, 2.5h, 2) benzene, reflux, 90 min

4: 1) O₃, 2) SMe₂ / 1) -78 deg C, 3 min, CH₂Cl₂, 0 deg C, 1h, 2) room temperature, 2h

With dmap; sodium hydroxide; dimethylsulfide; ozone; acetic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81659-8

Reference yield:

methyl (11S)-8α-hydroxy-11-phenylseleno-7αH-eudesm-4-en-12-oate (113306-93-7) → umbellifolide (89026-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / 0 °C

2: 1) 1M aqueous NaOH, / 1) EtOH, reflux, 2.5h, 2) benzene, reflux, 90 min

3: 1) O₃, 2) SMe₂ / 1) -78 deg C, 3 min, CH₂Cl₂, 0 deg C, 1h, 2) room temperature, 2h

With dmap; sodium hydroxide; dimethylsulfide; ozone; In dichloromethane;

DOI:10.1016/S0040-4020(01)81659-8

Reference yield:

11β-phenylseleno-7,8αH-eudesm-4-en-12,8-olide (113306-92-6) → umbellifolide (89026-40-4)

Guidance literature:

With dimethylsulfide; ozone; Yield given. Multistep reaction; 1) -78 deg C, 3 min, CH₂Cl₂, 0 deg C, 1h, 2) room temperature, 2h;

DOI:10.1016/S0040-4020(01)81659-8

upstream raw materials:

11β-phenylseleno-7,8αH-eudesm-4-en-12,8-olide

methyl (11S)-8α-hydroxy-11-phenylseleno-7αH-eudesm-4-en-12-oate

methyl (11S)-8α-mesyloxy-11-phenylseleno-7αH-eudesm-4-en-12-oate

11β-phenylseleno-7α,8βH-eudesm-4-en-12,8-olide

Refernces