gamma-Irone

Base Information

• Chemical Name: gamma-Irone
• CAS No.: 35124-16-4
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.328
• European Community (EC) Number: 201-218-0
• UNII: IOV6OG0LC8,IS4N6X2NA3
• Nikkaji Number: J1.724.137K,J427.507A
• Wikidata: Q22077110

Synonyms:(+)-(2R,6S)-cis-gamma-irone;(2R,6S)-irone

Chemical Property of gamma-Irone

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 206.167065321
• Heavy Atom Count: 15
• Complexity: 297

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(=C)C(C1(C)C)C=CC(=O)C
• Isomeric SMILES: C[C@@H]1CCC(=C)[C@@H](C1(C)C)/C=C/C(=O)C

Technology Process of gamma-Irone

There total 104 articles about gamma-Irone 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: 80.0%

methyllithium (917-54-4) + acide trans-(trimethyl-3,3,4 methylene cyclohexane-2 yl)-3 propenoique Δ2 trans (111923-59-2,111958-27-1,122046-56-4) → (+/-)-trans-γ-irone (79-68-5,35124-16-4,57129-08-5,72244-00-9,73365-47-6,82890-08-2,82890-09-3,89888-04-0,90242-86-7,101325-32-0,117894-47-0,127128-56-7,129314-22-3)

Guidance literature:

In diethyl ether; 1.) -20 deg C, 5 h, 2.) -5 deg C, 16 h;

DOI:10.1016/S0040-4020(01)89933-6

Reference yield: 62.0%

trans-3-(6-methylene-2,2,3-trimethylcyclohexyl)acrylonitrile + methyl iodide (74-88-4) → (+/-)-trans-γ-irone (79-68-5,35124-16-4,57129-08-5,72244-00-9,73365-47-6,82890-08-2,82890-09-3,89888-04-0,90242-86-7,101325-32-0,117894-47-0,127128-56-7,129314-22-3)

Guidance literature:

In diethyl ether; hexane; 2 h, -65 deg C; 1 h, 0 deg C;

Reference yield: 57.0%

4-(6-Methylene-2,2,3-trimethylcyclohexyl)-4-hydroxy-2-butanone (96641-42-8) → (+/-)-trans-γ-irone (79-68-5,35124-16-4,57129-08-5,72244-00-9,73365-47-6,82890-08-2,82890-09-3,89888-04-0,90242-86-7,101325-32-0,117894-47-0,127128-56-7,129314-22-3)

Guidance literature:

With aluminum oxide; In diethyl ether; Ambient temperature;

DOI:10.1246/bcsj.58.389

upstream raw materials:

Diethyl (2-oxopropyl)phosphonate

(-)-(1S,3R)-2,3,3-trimethyl-6-methylidenecyclohexane-1-carbaldehyde

methyllithium

(2,2,4-trimethyl-3-cyclohexen-1-yl)methanol

Downstream raw materials:

(+)-(2R)-β-irone

(-)-2R,6R-trans-α-irone

(-)-1t-(5c.6.6-trimethyl-2-methylene-cyclohexyl-(r))-buten-⁽¹⁾-one-⁽³⁾-(4-phenyl semicarbazone)

(+)-1-((1Ξ)-2,2,3c,6c-tetramethyl-cyclohexyl-(r))-butanone-(3)

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