Dihydroisoalantolactone

Base Information

• Chemical Name: Dihydroisoalantolactone
• CAS No.: 1856-58-2
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• DSSTox Substance ID: DTXSID60939983
• Nikkaji Number: J455.515E
• Wikidata: Q82916542
• Metabolomics Workbench ID: 144736
• ChEMBL ID: CHEMBL486423
• Mol file: 1856-58-2.mol

Synonyms:Dihydroisoalantolactone;1856-58-2;Decahydro-3,8a-dimethyl-5-methylenenaphtho(2,3-b)furan-2(3H)-one (3S-(3alpha,3abeta,4abeta,8aalpha,9abeta))-;Naphtho(2,3-b)furan-2(3H)-one, decahydro-3,8a-dimethyl-5-methylene-, (3S-(3alpha,3abeta,4abeta,8aalpha,9abeta))-;(3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylenedecahydronaphtho[2,3-b]furan-2(3H)-one;11,13-Dihydroisoalantolactone;CHEMBL486423;DTXSID60939983;CHEBI:191724;AKOS040751577;(3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one;3,8a-Dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one;(3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydro-3H-benzo[][1]benzouran-2-one

Chemical Property of Dihydroisoalantolactone

Chemical Property:

• Vapor Pressure: 3.26E-05mmHg at 25°C
• Melting Point: 171-172 °C
• Boiling Point: 354.8°Cat760mmHg
• Flash Point: 148°C
• PSA: 26.30000
• Density: 1.06g/cm³
• LogP: 3.32050
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 373

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC3C(=C)CCCC3(CC2OC1=O)C
• Isomeric SMILES: C[C@H]1[C@H]2C[C@H]3C(=C)CCC[C@@]3(C[C@H]2OC1=O)C

Technology Process of Dihydroisoalantolactone

There total 43 articles about Dihydroisoalantolactone 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: 91.0%

2,3,3aβ,4,4aα,5,6,7,8,8a,9,9aβ-dodecahydro-3,8aβ-dimethyl-5-methylenenaphtho<2,3-b>furan-3-carboxylic acid methyl ester (73483-65-5,73483-66-6) → (+/-)-dihydrocallitrisin (1856-58-2,22415-07-2,58511-33-4,66964-61-2,72523-74-1,77480-20-7,77480-21-8,108667-51-2)

Guidance literature:

With sodium cyanide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 80 ℃; for 1h;

DOI:10.1021/ja00527a046

Reference yield:

isoalantolactone (470-17-7) → 11,13-dihydroisoalantolactone (1856-58-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / ethanol / 2 h / Ambient temperature

2: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / -15 - -5 °C

3: 1.) trifluoroacetic anhydride, 2.) triethylamine / 1.) CH₂Cl₂, RT, 3 h, 2.) CH₂Cl₂, RT, 2 h

4: 70 mg / oxone / tetrahydrofuran; H₂O / 72 h / Ambient temperature

5: 18 percent / NaBH₄ / tetrahydrofuran; D₂O / 0.25 h / Ambient temperature; other vinyl sulfoxides, other reagents, other solvents, var. time

With Oxone; sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; dichloromethane; water; water-d2;

DOI:10.1021/jo00287a024

Reference yield:

isoalantolactone → 11,13-dihydroisoalantolactone (1856-58-2)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; for 0.25h; Reagent/catalyst;

DOI:10.14233/ajchem.2017.20254

upstream raw materials:

isoalantolactone

2,3,3aβ,4,4aα,5,6,7,8,8a,9,9aβ-dodecahydro-3,8aβ-dimethyl-5-methylenenaphtho<2,3-b>furan-3-carboxylic acid methyl ester

(3aβ,4aβ,8aβ,9aβ)-3a,4,4a,5,6,8,8a,9,9a-decahydro-8a-methyl-5-methylenenaphtho<2,3-b>furan-2(3H)-one

methyl iodide

Downstream raw materials:

(3aR,4aS,8aR,9aR)-3-[1-Benzenesulfinyl-meth-(Z)-ylidene]-8a-methyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one

(3aR,4aS,8aR,9aR)-3-[1-Benzenesulfinyl-meth-(E)-ylidene]-8a-methyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one

(3aR,4aS,8aR,9aR)-8a-Methyl-5-methylene-3-[1-phenylsulfanyl-meth-(Z)-ylidene]-decahydro-naphtho[2,3-b]furan-2-one

(3aR,4aS,8aR,9aR)-8a-Methyl-5-methylene-3-[1-phenylsulfanyl-meth-(E)-ylidene]-decahydro-naphtho[2,3-b]furan-2-one