Sinularic acid A

Base Information

• Chemical Name: Sinularic acid A
• CAS No.: 118583-94-1
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.457
• Mol file: 118583-94-1.mol

Synonyms:Sinularic acid A;118583-94-1;3,7,11-Cyclotetradecatriene-1-acetic acid, 4,8,12-trimethyl-alpha-methylene-, (R-(E,E,E))-

Chemical Property of Sinularic acid A

Chemical Property:

• Vapor Pressure: 1.51E-09mmHg at 25°C
• Boiling Point: 455.1°Cat760mmHg
• Flash Point: 344.1°C
• Density: 0.938g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 492

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CCC(CCC(=CCC1)C)C(=C)C(=O)O)C
• Isomeric SMILES: C/C/1=C/CC/C(=C\C[C@@H](CC/C(=C\CC1)/C)C(=C)C(=O)O)/C

Technology Process of Sinularic acid A

There total 17 articles about Sinularic acid A 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: 65.0%

2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal (118607-64-0) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propanoic acid (118583-94-1)

Guidance literature:

With calcium hypochlorite; acetic acid; In acetonitrile; at 15 ℃; for 20h;

DOI:10.1016/S0957-4166(99)00194-9

Reference yield:

trans-geranyl bromide (6138-90-5) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propanoic acid (118583-94-1)

Guidance literature:

Multi-step reaction with 13 steps

1: dimethylformamide / 24 h / Ambient temperature

2: 78 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 25 h / 20 °C

3: 1.) Ti(OiPr)4, CaH₂, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, toluene, -40 deg C, 5 h

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h

5: 78 percent / Li, EtNH₂ / tetrahydrofuran / 4 h / -78 °C

6: 1.) Ph₃P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h

7: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C

8: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C

9: Bu₄N₊F_- / tetrahydrofuran / 24 h / 15 °C

10: 70 percent / Li, EtNH₂ / tetrahydrofuran / 3.5 h / -78 °C

11: 49 percent / SOCl₂, pyridine / 3 h / 15 °C

12: 92 percent / MnO₂ / hexane / 12 h / 15 °C

13: 65 percent / 67 percent aq. Ca(ClO)2, glacial acetic acid / acetonitrile / 20 h / 15 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; N-chloro-succinimide; calcium hypochlorite; selenium(IV) oxide; thionyl chloride; calcium hydride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; lithium; ethylamine; acetic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(99)00194-9

Reference yield:

Geraniol (106-24-1) → 2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propanoic acid (118583-94-1)

Guidance literature:

Multi-step reaction with 14 steps

1: PBr₃ / diethyl ether / 3 h / 20 °C

2: dimethylformamide / 24 h / Ambient temperature

3: 78 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 25 h / 20 °C

4: 1.) Ti(OiPr)4, CaH₂, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, toluene, -40 deg C, 5 h

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h

6: 78 percent / Li, EtNH₂ / tetrahydrofuran / 4 h / -78 °C

7: 1.) Ph₃P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h

8: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C

9: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C

10: Bu₄N₊F_- / tetrahydrofuran / 24 h / 15 °C

11: 70 percent / Li, EtNH₂ / tetrahydrofuran / 3.5 h / -78 °C

12: 49 percent / SOCl₂, pyridine / 3 h / 15 °C

13: 92 percent / MnO₂ / hexane / 12 h / 15 °C

14: 65 percent / 67 percent aq. Ca(ClO)2, glacial acetic acid / acetonitrile / 20 h / 15 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; N-chloro-succinimide; calcium hypochlorite; selenium(IV) oxide; thionyl chloride; calcium hydride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; phosphorus tribromide; lithium; ethylamine; acetic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(99)00194-9

upstream raw materials:

2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal

trans-geranyl bromide

Geraniol

3,7-dimethyl-2E,6-octadien-1-yl acetate

Downstream raw materials:

(+)-sinulariol-D

2-<1R,4,8,12-trimethyl-3E,7E,11E-cyclotertadecatrien-1-yl>propenal

Refernces