Decaline

Base Information

• Chemical Name: Decaline
• CAS No.: 14727-56-1
• Molecular Formula: C₂₆H₃₁NO₅
• Molecular Weight: 437.536
• DSSTox Substance ID: DTXSID00933086
• Wikidata: Q27106344
• Mol file: 14727-56-1.mol

Synonyms:Decaline;14727-56-1;(12S,14S,19AS)-24,25-dimethoxy-11,13,14,16,17,18,19,19a-octahydro-12H-3,8-dioxa-1(4,2)-quinolizina-2(1,2),4(1,4)-dibenzenacyclooctaphan-7-one;(12S,19aS)-24,25-dimethoxy-11,13,14,16,17,18,19,19a-octahydro-12H-3,8-dioxa-1(4,2)-quinolizina-2(1,2)-benzena-4(1,4)-cyclohexanacyclooctaphan-7-one;6,9-etheno-14,21-methano-12H,14H,21H-pyrido(2,1-l)(1,9,13)benzodioxaazacyclohexadecin-12-one, 10,11,15,15a,16,17,18,19-octahydro-2,3-dimethoxy-, (14S-(14R*,15aR*,21R*))-;starbld0040944;SCHEMBL22723;CHEBI:4345;DTXSID00933086;AKOS040751471;Q27106344;(9S,15S,17S)-5,6-dimethoxy-2,18-dioxa-10-azapentacyclo[20.2.2.19,17.03,8.010,15]heptacosa-1(24),3,5,7,22,25-hexaen-19-one;6,9-Etheno-14,21-methano-12H,14H,21H-pyrido[2,1-l][1,9,13]benzodioxaazacyclohexadecin-12-one, 10,11,15,15a,16,17,18,19-octahydro-2,3-dimethoxy-, (14S,15aS,21S)-;8,9-Dimethoxy-1,3,4,16,17,20,21,21a-octahydro-2H,6H,18H-12,15-etheno-6,20-methanopyrido[2,1-l][1,9,13]benzodioxazacyclohexadecin-18-one

Chemical Property of Decaline

Chemical Property:

• Vapor Pressure: 5.07E-14mmHg at 25°C
• Boiling Point: 592.7°Cat760mmHg
• Flash Point: 312.3°C
• Density: 1.25g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 437.22022309
• Heavy Atom Count: 32
• Complexity: 636

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C3CC(CC4N3CCCC4)OC(=O)CCC5=CC=C(O2)C=C5)OC
• Isomeric SMILES: COC1=C(C=C2C(=C1)[C@@H]3C[C@H](C[C@H]4N3CCCC4)OC(=O)CCC5=CC=C(O2)C=C5)OC

Technology Process of Decaline

There total 3 articles about Decaline 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: 28.4%

3-{4-[2-((2R,4S,9aS)-2-Hydroxy-octahydro-quinolizin-4-yl)-4,5-dimethoxy-phenoxy]-phenyl}-propionic acid (50650-81-2,53425-29-9,55515-74-7,97415-37-7) → (+/-)-decaline (14727-56-1,32886-91-2,50412-65-2,53494-86-3) + Formic acid (2R,4S,9aS)-4-{2-[4-(2-dimethylcarbamoyl-ethyl)-phenoxy]-4,5-dimethoxy-phenyl}-octahydro-quinolizin-2-yl ester (97387-82-1)

Guidance literature:

With N,N-dimethylformamide dineopentyl acetal; In toluene; for 12h; Heating;

DOI:10.1248/cpb.33.532

Reference yield: 9.7%

3-{4-[2-((2R,4S,9aS)-2-Hydroxy-octahydro-quinolizin-4-yl)-4,5-dimethoxy-phenoxy]-phenyl}-propionic acid (50650-81-2,53425-29-9,55515-74-7,97415-37-7) + N,N-dimethylformamide dineopentyl acetal (4909-78-8) → (+/-)-decaline (14727-56-1,32886-91-2,50412-65-2,53494-86-3) + Formic acid (2R,4S,9aS)-4-{2-[4-(2-dimethylcarbamoyl-ethyl)-phenoxy]-4,5-dimethoxy-phenyl}-octahydro-quinolizin-2-yl ester (97387-82-1)

Guidance literature:

In toluene; for 12h; Heating;

DOI:10.1248/cpb.33.532

Reference yield:

3-(4-hydroxyphenyl)propionic acid methyl ester (5597-50-2) → (+/-)-decaline (14727-56-1,32886-91-2,50412-65-2,53494-86-3)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃, CuO / pyridine / 5 h / 120 - 150 °C

2: 99 percent / HgO / CH₂Cl₂ / 1.5 h / Heating

3: 1) methanesulfonyl chloride 2) Zn / 1) CH₂Cl₂, 0 deg C, 1.2 h; 2) aq. AcOH, room temp., 2.5 h

4: 77.2 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 3.75 h / Ambient temperature

5: LiOH / methanol; H₂O / 2 h / Ambient temperature

6: 57.4 percent / 2,2'-dipyridyl disulfide, triphenylphosphine / CH₂Cl₂ / 1 h / Ambient temperature

With lithium hydroxide; 2,2'-dipyridyldisulphide; potassium carbonate; methanesulfonyl chloride; triphenylphosphine; copper(II) oxide; mercury(II) oxide; zinc; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

DOI:10.1248/cpb.33.532

upstream raw materials:

3-{4-[2-((2R,4S,9aS)-2-Hydroxy-octahydro-quinolizin-4-yl)-4,5-dimethoxy-phenoxy]-phenyl}-propionic acid

N,N-dimethylformamide dineopentyl acetal

3-(4-hydroxyphenyl)propionic acid methyl ester