(6R)-dehydrovomifoliol

Base Information

• Chemical Name: (6R)-dehydrovomifoliol
• CAS No.: 39763-38-7
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• UNII: PQ5ZZ67JLZ
• DSSTox Substance ID: DTXSID501140050
• Nikkaji Number: J2.747.724K,J488.896K
• Wikidata: Q27121513
• Metabolomics Workbench ID: 57244
• Mol file: 39763-38-7.mol

Synonyms:(6R)-dehydrovomifoliol;Dehydrovomifoliol, (-)-;PQ5ZZ67JLZ;(R)-(-)-Dehydrovomifoliol;(-)-dehydrovomifoliol;UNII-PQ5ZZ67JLZ;39763-38-7;C13H18O3;2-Cyclohexen-1-one, 4-hydroxy-3,5,5-trimethyl-4-((1E)-3-oxo-1-buten-1-yl)-, (4R)-;2-Cyclohexen-1-one, 4-hydroxy-3,5,5-trimethyl-4-(3-oxo-1-butenyl)-, (R-(E))-;(4R)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one;(6R)-6-hydroxy-3-oxo-alpha-ionone;(-)-Dihydrovomifoliol;(?)-Dehydrovomifoliol;CHEBI:49177;DTXSID501140050;(+-)-6-hydroxy-3-oxo-alpha-ionone;(4R)-4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one;Q27121513;(6R)-6-Hydroxy-1,5,5-trimethyl-6-(3-oxo-1-butenyl)cyclohexene-3-one;(4R)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxo-1-buten-1-yl]-2-cyclohexen-1-one

Chemical Property of (6R)-dehydrovomifoliol

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)CC(C1(C=CC(=O)C)O)(C)C
• Isomeric SMILES: CC1=CC(=O)CC([C@@]1(/C=C/C(=O)C)O)(C)C

Technology Process of (6R)-dehydrovomifoliol

There total 3 articles about (6R)-dehydrovomifoliol 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:

(3R,6S)-3,6-dihydroxy-α-ionone (39763-31-0) → (6S,7E)-6-hydroxy-4,7-megastigmadien-3,9-dione (39763-38-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2007.10.014

Reference yield:

(R)-4-Hydroxy-3,5,5-trimethyl-4-vinyl-cyclohex-2-enone (124062-61-9) → (6S,7E)-6-hydroxy-4,7-megastigmadien-3,9-dione (39763-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / O₃, Me₂S / CH₂Cl₂; pyridine / 0.33 h / -78 °C

2: 75 percent

With dimethylsulfide; ozone; In pyridine; dichloromethane;

DOI:10.1016/S0040-4039(00)99568-6

Reference yield:

(3S,5S,6R)-3-acetoxy-5,6-epoxy-5,6-dihydro-β-ionon (50281-40-8) → (6S,7E)-6-hydroxy-4,7-megastigmadien-3,9-dione (39763-38-7)

Guidance literature:

Multistep reaction; (i) KOH, MeOH, (ii) CrO₃, Py;

DOI:10.1016/S0040-4020(01)97270-9

upstream raw materials:

(3S,5S,6R)-3-acetoxy-5,6-epoxy-5,6-dihydro-β-ionon

(3R,6S)-3,6-dihydroxy-α-ionone

(R)-4-Hydroxy-3,5,5-trimethyl-4-vinyl-cyclohex-2-enone