Solanone

Base Information

• Chemical Name: Solanone
• CAS No.: 1937-54-8
• Molecular Formula: C₁₃H₂₂O
• Molecular Weight: 194.317
• UNII: 233MY0C8V7
• DSSTox Substance ID: DTXSID201025643
• Nikkaji Number: J161.348K
• Wikipedia: Solanone
• Wikidata: Q10861391
• Mol file: 1937-54-8.mol

Synonyms:Solanone;1937-54-8;6,8-Nonadien-2-one, 8-methyl-5-(1-methylethyl)-, (5S,6E)-;UNII-233MY0C8V7;233MY0C8V7;(5S,6E)-8-methyl-5-propan-2-ylnona-6,8-dien-2-one;(S,E)-5-Isopropyl-8-methylnona-6,8-dien-2-one;L-(+)-2-methyl-5-isopropyl-1,3-nonadien-8-one;(5S,6E)-8-Methyl-5-(1-methylethyl)-6,8-nonadien-2-one;6,8-Nonadien-2-one, 8-methyl-5-(1-methylethyl)-, (S-(E))-;6,8-Nonadien-2-one, 8-methyl-5-(1-methylethyl)-, [S-(E)]-;SOLANONE [MI];SCHEMBL322675;PQDRXUSSKFWCFA-CFNZNRNTSA-N;DTXSID201025643;Q10861391;(5S,6E)-8-methyl-5-(propan-2-yl)nona-6,8-dien-2-one;6,8-Nonadien-2-one, 5-isopropyl-8-methyl-, (E)-(R)-()-

Chemical Property of Solanone

Chemical Property:

• Vapor Pressure: 0.00743mmHg at 25°C
• Refractive Index: nD20 1.4755
• Boiling Point: 269°C at 760 mmHg
• Flash Point: 96.3°C
• PSA: 17.07000
• Density: 0.846g/cm³
• LogP: 3.76010
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 194.167065321
• Heavy Atom Count: 14
• Complexity: 223

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCC(=O)C)C=CC(=C)C
• Isomeric SMILES: CC(C)[C@H](CCC(=O)C)/C=C/C(=C)C
• Uses: Solanone is use as a flavoring agent in cigarettes. The compound can be optioned from Nicotiana glutinosa L. leaves.

Technology Process of Solanone

There total 16 articles about Solanone 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: 75.0%

2-bromoprop-1-ene (557-93-7) + (S,E)-7-bromo-5-isopropylhept-6-en-2-one → solanone (1937-54-8,99745-11-6)

Guidance literature:

With bis(acetylacetonate)nickel(II); bathophenanthroline; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc; In N,N-dimethyl acetamide; at 30 ℃; for 10h; Schlenk technique; Inert atmosphere;

Reference yield: 66.0%

2-bromoprop-1-ene (557-93-7) + (S,E)-7-bromo-5-isopropylhept-6-en-2-one → solanone (1937-54-8,99745-11-6) + C20H34O2

Guidance literature:

With NiBr₂* 4,7-diphenyl-1,10-phenanthroline; tetra-(n-butyl)ammonium iodide; magnesium chloride; zinc; In N,N-dimethyl acetamide; at 25 ℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1039/d1ob00791b

Reference yield: 55.0%

diethyl (2-methylallyl)phosphonate (51533-70-1) + (S)-2-isopropyl-5-carbonylhexanal (57213-53-3) → solanone (1937-54-8,99745-11-6)

Guidance literature:

diethyl (2-methylallyl)phosphonate; With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; In tetrahydrofuran; tert-butyl methyl ether; at -78 ℃; for 0.5h;

(S)-2-isopropyl-5-carbonylhexanal; In tetrahydrofuran; tert-butyl methyl ether; at -78 - 20 ℃; for 16h;

upstream raw materials:

(S)-5-Isopropyl-hept-6-yn-2-one

2-((S)-3-Isopropyl-pent-4-ynyl)-2-methyl-[1,3]dioxolane

diethyl (2-methylallyl)phosphonate

(S)-2-isopropyl-5-carbonylhexanal

Refernces

• 1、 -. "Diene compound and synthesis method thereof". Paragraph 0055-0062. . Retrieved 2021/07/28.
• 2、 -. "(E)-type solanone and preparation method and application thereof". Paragraph 0032-0035. . Retrieved 2020/05/02.