beta-Irone

Base Information

• Chemical Name: beta-Irone
• CAS No.: 72074-84-1
• Molecular Formula: C14H22O
• Molecular Weight: 206.328
• European Community (EC) Number: 201-220-1
• UNII: W8NW93JQ9H
• DSSTox Substance ID: DTXSID70861640
• Nikkaji Number: J1.653.769A,J4.240D
• Wikidata: Q27292468
• Mol file: 72074-84-1.mol

Synonyms:beta-Irone;6-Methyl-.beta.-ionone;.beta.-Irone;79-70-9;W8NW93JQ9H;beta-Irone [MI];3-Buten-2-one, 4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-;6-Methyl-beta-ionone;(+/-)-beta-irone;beta-Ionone, 6-methyl-;BETA-N-METHYLIONONE;UNII-W8NW93JQ9H;beta-Irone, (+/-)-;.beta.-Ionone, 6-methyl-;4-(2,5,6,6-Tetramethyl-1-cyclohexen-1-yl)-3-buten-2-one;EINECS 201-220-1;4-(2,5,6,6-Tetramethyl-1-cyclohexenyl)but-3-en-2-one;4-(2,5,6,6-Tetramehtyl-1-cyclohexenyl)-3-buten-2-one;3-Buten-2-one, 4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-, (3E)-;72074-84-1;2-Methyl-.beta.-ionone;.BETA.-IRONE [MI];SCHEMBL873116;DTXSID70861640;(+/-)-.BETA.-IRONE;.BETA.-IRONE, (+/-)-;Q27292468;4-(2,5,6,6-tetramethylcyclohexen-1-yl)but-3-en-2-one;(E)-4-(2,5,6,6-tetramethylcyclohex-1-enyl)but-3-en-2-one;4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-3-buten-2-on;4-(2,5,6,6-Tetramethyl-1-cyclohexen-1-yl)-3-buten-2-one #;(E)-4-(2alpha,5,6,6-Tetramethyl-1-cyclohexene-1-yl)-3-butene-2-one;4 - (2,5,6,6 - tetramethyl - 1 - cyclohexen - 1 - yl) - 3 - buten - 2 - one

Chemical Property of beta-Irone

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 206.167065321
• Heavy Atom Count: 15
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=C(C1(C)C)C=CC(=O)C)C
• Isomeric SMILES: CC1CCC(=C(C1(C)C)/C=C/C(=O)C)C

Technology Process of beta-Irone

There total 29 articles about beta-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: 84.0%

4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone (72049-77-5,72049-78-6) → beta-irone (72074-84-1)

Guidance literature:

With sodium methylate; In tetrahydrofuran; tert-butyl alcohol; Ambient temperature; 1) 5 grad C, 2) 7 h, RT;

DOI:10.1021/jo01289a003

Reference yield: 39.0%

2,5,6,6-tetramethylcyclohex-1-enecarbaldehyde (31162-52-4) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → beta-irone (72074-84-1)

Guidance literature:

In dichloromethane; at 70 ℃; under 10500800 Torr;

DOI:10.1007/BF01168096

Reference yield:

(3E,5Ξ)-6,9,10-trimethyl-undeca-3,5,9-trien-2-one (645-68-1,6754-31-0,52612-57-4,52612-58-5,78478-83-8,78478-84-9) → 1-(1,3,4-trimethyl-3-cyclohexenyl)-1-penten-4-one (162282-94-2) + gamma-irone (79-68-5) + beta-irone (72074-84-1) + (1'RS,5'RS)-4-(2',5',6',6'-tetramethylcyclohex-2'-enyl)butan-2-one (81456-93-1,124886-67-5,124886-68-6,132437-12-8,132437-13-9) + (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on (72074-86-3,54082-69-8)

Guidance literature:

With phosphoric acid; In toluene; at 110 ℃; for 1h; Mechanism;

upstream raw materials:

pseudoirone

(+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on

4-(2,5,6,6-Tetramethylcyclohexenyl)-4-(phenylsulfonyl)-2-butanone

(3E)-6,9,10-trimethylundeca-3,5,8-trien-2-one

Downstream raw materials:

(+/-)-4t-(2,5,6,6-tetramethyl-cyclohex-1-enyl)-but-3-en-2-one-(4-[1]naphthyl semicarbazone)

(+/-)-4t-(2,5,6,6-tetramethyl-cyclohex-1-enyl)-but-3-en-2-one-(2,4-dinitro-phenylhydrazone); (+/-)-trans-β-iron-(2,4-dinitro-phenylhydrazone)

4-(2,5,6,6-tetramethyl-1-cyclohexene-1-yl)-3-butane-2-one

2,5,6,6-tetramethylcyclohex-1-enecarbaldehyde