Widdrol

Base Information

• Chemical Name: Widdrol
• CAS No.: 6892-80-4
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.371
• DSSTox Substance ID: DTXSID50988627
• Nikkaji Number: J15.581K
• Wikidata: Q82977253
• Metabolomics Workbench ID: 127541
• ChEMBL ID: CHEMBL2253133
• Mol file: 6892-80-4.mol

Synonyms:widdrol

Chemical Property of Widdrol

Chemical Property:

• Vapor Pressure: 8.86E-05mmHg at 25°C
• Melting Point: 98 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 303.5°C at 760 mmHg
• PKA: 14.98±0.60(Predicted)
• Flash Point: 128.4°C
• PSA: 26.30000
• Density: 0.96g/cm³
• LogP: 3.98610
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 315

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1=CCC(CC2)(C)O)C)C
• Isomeric SMILES: C[C@@]12CCCC(C1=CC[C@@](CC2)(C)O)(C)C

Technology Process of Widdrol

There total 62 articles about Widdrol 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: 96.0%

Acetic acid (4aR,7R)-1,1,4a,7-tetramethyl-2,3,4,4a,5,6,7,8-octahydro-1H-benzocyclohepten-7-yl ester (70069-94-2,107381-12-4) → (+/-)-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.5h;

DOI:10.1016/S0040-4020(01)87741-3

Reference yield: 78.0%

<4aR*,7S*,8R*>-7,8-epoxy-2,3,4,4a,5,6,7,8,-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene (116914-10-4) → (+/-)-epi-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

With lithium aluminium tetrahydride; In 1,2-dimethoxyethane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87742-5

Reference yield:

(5aS,9aR)-5a,9,9-Trimethyl-9a-vinyl-octahydro-benzo[b]oxepin-2-one (75154-34-6) → (+/-)-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

2: lithium diisopropylamide / hexamethylphosphoric acid triamide; tetrahydrofuran

3: 2.) tetra-n-butylammonium fluoride / 1.) toluene, 11o deg C, 10 h

4: 1.) SOCl₂, 2.) MCPBA, 3.) LAH

With lithium aluminium tetrahydride; thionyl chloride; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ja00542a059

upstream raw materials:

Widdrol-epoxid

cobalt(III) acetate

thujopsene

(1aR,2S,4aS,8aS)-2-Chloro-2,4a,8,8-tetramethyl-decahydro-cyclopropa[d]naphthalene

Downstream raw materials:

1,1,3-Trimethyl-3-(3,5-dihydroxy-3-methyl-pentyl)-cyclohexanol-⁽²⁾