Windaus Ketone

Base Information

• Chemical Name: Windaus Ketone
• CAS No.: 55812-80-1
• Molecular Formula: C₁₉H₃₂O
• Molecular Weight: 276.462
• DSSTox Substance ID: DTXSID10453987
• Nikkaji Number: J1.158.145E
• Wikidata: Q82275297
• Mol file: 55812-80-1.mol

Synonyms:Windaus Ketone;55812-80-1;(1R,3aR,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one;(1R,3aR,7aR)-1-((2R,5R,E)-5,6-Dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-one;(1R,3aR,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-one;starbld0014473;SCHEMBL14489185;DTXSID10453987;CS-0005989;E80839;(3aalpha)-1beta-[(1R,2E,4R)-1,4,5-Trimethyl-2-hexenyl]-7abeta-methylhydrindane-4-one;(1R,3aR,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-one

Chemical Property of Windaus Ketone

Chemical Property:

• PSA: 17.07000
• LogP: 5.25630
• Storage Temp.: -20?C Freezer
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 276.245315640
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

97% ^*data from raw suppliers

WindausKetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=O)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CCCC2=O)C
• Uses: Windaus Ketone is an intermediate used in the preparation of Vitamin D derivatives.

Technology Process of Windaus Ketone

There total 4 articles about Windaus Ketone 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: 83.0%

(5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol (131852-63-6) → (1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) + (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one (55812-80-1,55870-05-8,70144-73-9) + (2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol (96685-53-9)

Guidance literature:

(5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol; With pyridine; lead(IV) acetate; In dichloromethane; at 0 ℃; for 0.25h;

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.25h;

DOI:10.1055/s-1999-3530

Reference yield: 63.0%

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol (343969-47-1) → (1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) + (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one (55812-80-1,55870-05-8,70144-73-9) + (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol (338956-81-3)

Guidance literature:

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol; With pyridine; lead(IV) acetate; In dichloromethane; at 0 ℃; for 1.5h;

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 1.5h;

Reference yield:

Calciferol (50-14-6) → (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one (55812-80-1,55870-05-8,70144-73-9) + [(S)-5-Hydroxy-2-methylene-cyclohex-(Z)-ylidene]-acetaldehyde

Guidance literature:

Multi-step reaction with 2 steps

1: potassium permanganate / tetrahydrofuran; water

2: lead(IV) tetraacetate / dichloromethane

With potassium permanganate; lead(IV) tetraacetate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bmcl.2012.05.037

upstream raw materials:

(5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol

(1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol

Calciferol

(3S,5Z,7Ξ)-9,10-seco-8ξ-ergosta-5,10(19),22t-triene-3,7,8-triol

Downstream raw materials:

<(1Z),(5S)>-2-<5-hydroxy-2-methylcyclohexylidene>-ethanol

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol

(1R,3aS,5S,7aR)-7a-Methyl-5-((S)-1-methyl-4-oxo-cyclohex-2-enyl)-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one

(1R,2S,5S)-5-Methoxymethoxy-2-methyl-2-[(1R,3aS,5S,7aR)-7a-methyl-4-oxo-1-((Z)-(R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-5-yl]-cyclohexanecarbonitrile