(s)-alpha-Damascone

Base Information

• Chemical Name: (s)-alpha-Damascone
• CAS No.: 116497-11-1
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.301
• DSSTox Substance ID: DTXSID401182857
• Nikkaji Number: J604.214G
• Mol file: 116497-11-1.mol

Synonyms:(s)-alpha-damascone;SCHEMBL11449382;DTXSID401182857;(2E)-1-[(1S)-2,6,6-Trimethyl-2-cyclohexen-1-yl]-2-buten-1-one;116497-11-1

Chemical Property of (s)-alpha-Damascone

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.151415257
• Heavy Atom Count: 14
• Complexity: 282

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CC(=O)C1C(=CCCC1(C)C)C
• Isomeric SMILES: C/C=C/C(=O)[C@@H]1C(=CCCC1(C)C)C

Technology Process of (s)-alpha-Damascone

There total 27 articles about (s)-alpha-Damascone 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: 95.0%

(-)-(6S,9S)-7-oxo-α-dihydroionol acetate (908297-89-2) → (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one (116497-11-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2006.05.024

Reference yield: 86.0%

[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-1-one (174198-90-4) → (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one (116497-11-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 22 ℃; for 12h;

DOI:10.1021/jo049012j

Reference yield: 84.0%

(S)-α-damascol (28102-24-1,28102-25-2,52610-46-5,145774-37-4,148021-15-2,148021-16-3) → (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one (116497-11-1)

Guidance literature:

With manganese(IV) oxide; In acetone;

upstream raw materials:

2,6,6-trimethylcyclohex-2-en-1-ylidene ketene

allylmagnesium bromide

(S)-2,6,6-Trimethyl-cyclohex-2-enecarbothioic acid S-phenyl ester

(S)-α-damascol

Downstream raw materials:

2,2-Dimethyl-propionic acid 3-benzyloxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester

2,2-Dimethyl-propionic acid 3-oxo-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester

2,2-Dimethyl-propionic acid 3-hydroxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butyl ester

3-Benzyloxy-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butan-1-ol