Wieland-Miescher ketone

Base Information

• Chemical Name: Wieland-Miescher ketone
• CAS No.: 20007-72-1
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.231
• Hs Code.: 2914690090
• European Community (EC) Number: 243-463-6
• NSC Number: 87581
• UNII: FAX7VUD577
• DSSTox Substance ID: DTXSID40894783
• Nikkaji Number: J280.421B
• Wikipedia: Wieland%E2%80%93Miescher_ketone
• Wikidata: Q413602
• ChEMBL ID: CHEMBL1891117
• Mol file: 20007-72-1.mol

Synonyms:Wieland-Miescher ketone;20007-72-1;1,6(2H,7H)-Naphthalenedione, 3,4,8,8a-tetrahydro-8a-methyl-;WIELAND-MIESCHERKETONE;8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione;3,4,8,8a-Tetrahydro-8a-methyl-(2H,7H)naphthalene-1,6-dione;FAX7VUD577;MLS002694757;9-Methyl-delta-5(10)-octaline-1,6-dione;8a-methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione;EINECS 243-463-6;NSC-87581;3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione;8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione;(+/-)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione;NSC87581;MODX;Wieland-Michler ketone;9-Methyl-5(10)-oCtaline-1,6-dione;Wieland-Miescher-Keton;9(S)-Methyl-delta-5(10)-octalin-1,6-dione;9-(S)-Methyl-.delta.-5(10)-octalin-1,6-dione;UNII-FAX7VUD577;SCHEMBL260976;8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione #;CHEMBL1891117;DTXSID40894783;HMS3094C09;8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione;MFCD00001687;NSC 87581;STL556166;(R/S)-WIELAND-MIESCHER KETONE;8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione (racemic);AKOS015916750;(+/-)-WIELAND-MIESCHER KETONE;9-Methyl-delta5,10-octalin-1,6-dione;AS-70912;SMR001560678;9-Methyl-delta5(10)-octalin-1,6-dione;9-Methyl-.delta.5(10)-octalin-1,6-dione;FT-0604485;FT-0605259;FT-0637936;FT-0642420;9-METHYL-5(10)-OCTALIN-1,6-DIONE;(+/-)-9-Methyl-5(10)-octaline-1,6-dione;A814160;Q413602;9-METHYL-.DELTA.5,10-OCTALIN-1,6-DIONE;J-640319;8a-Methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione;9-METHYL-1,6-DIOXO-1,2,3,4,6,7,8,9-OCTAHYDRONAPHTHALENE;(+/-)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione;(+/-)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione, 98%;(+/-)-8A-METHYL-1,2,3,4,6,7,8,8A-OCTAHYDRO-1,6-NAPHTHALENEDIONE;8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione;Wieland-Miescher ketone, racemic

Chemical Property of Wieland-Miescher ketone

Chemical Property:

• Appearance/Colour: BEIGE TO BROWN ADHERING CRYSTALLINE POWDER
• Vapor Pressure: 0.000229mmHg at 25°C
• Melting Point: 47-50ºC(lit.)
• Refractive Index: 1.5010 (estimate)
• Boiling Point: 325.5ºC at 760 mmHg
• Flash Point: 122 ºC
• PSA: 34.14000
• Density: 1.1 g/cm³
• LogP: 2.03500
• Storage Temp.: 0-6°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

(±)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCCC2=O

Technology Process of Wieland-Miescher ketone

There total 22 articles about Wieland-Miescher ketone 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%

3-hydroxy-2-methyl-1-cyclohexanone (102547-88-6) + methyl vinyl ketone (78-94-4,25038-87-3) → Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1)

Guidance literature:

at 185 ℃; for 6h;

Reference yield: 78.0%

2-methylcyclohexane-1,3-dione (1193-55-1) + methyl vinyl ketone (78-94-4,25038-87-3) → 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione (5073-65-4) + Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) + 2-acetyl-6-methyl-2,3-dihydropyran (28450-02-4)

Guidance literature:

magnesium oxide; at 100 ℃; for 2h; under 75007.5 Torr;

DOI:10.1016/j.tetlet.2004.04.146

Reference yield: 73.0%

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione (5073-65-4) → Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1)

Guidance literature:

With pyrrolidine; In toluene; for 2h; Dean-Stark; Reflux; Inert atmosphere;

DOI:10.1002/anie.202111639

upstream raw materials:

2-methylcyclohexane-1,3-dione

acetonedicarboxylic acid

4-(diethylamino)butan-2-one

diethyl-methyl-(3-oxo-butyl)-ammonium; iodide

Downstream raw materials:

4a-methyl-5-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-4,4a,7,8-tetrahydronaphthalen-2(3H)-one

8a-methyl-6-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-3,7,8,8a-tetrahydronaphthalen-1(2H)-one

8a-methyl-3,8-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-1,2,6,8a-tetrahydronaphthalen

γ-<3-Keto-6-methylcyclohexen-(1)-yl-(1)>-buttersaeuremethylester

Refernces

• 1、 Perni, Robert B.,Gribble, Gordon W.. "A synthetic approach to (±)-aristomakine". . p. 75 - 84. Retrieved 2018/07/03.
• 2、 Zhang, Xiao-Ming,Wang, Min,Tu, Yong-Qiang,Fan, Chun-An,Jiang, Yi-Jun,Zhang, Shu-Yu,Zhang, Fu-Min. "Prolinamide/PPTS-catalyzed Hajos-Parrish annulation: Efficient approach to the tricyclic core of cylindricine-type alkaloids". scheme or table. p. 2831 - 2835. Retrieved 2009/05/07.