Alliacol A

Base Information

• Chemical Name: Alliacol A
• CAS No.: 79232-29-4
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• DSSTox Substance ID: DTXSID80229590
• Nikkaji Number: J34.172J
• Wikidata: Q77562126
• Metabolomics Workbench ID: 144096
• Mol file: 79232-29-4.mol

Synonyms:alliacol A

Chemical Property of Alliacol A

Chemical Property:

• Vapor Pressure: 4.58E-10mmHg at 25°C
• Boiling Point: 451.9°C at 760 mmHg
• Flash Point: 171.4°C
• PSA: 59.06000
• Density: 1.28g/cm³
• LogP: 1.56670
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 524

Purity/Quality:

95%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2(C(=C)C(=O)OC23C14C(O4)C(C3)(C)C)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(C(=C)C(=O)O[C@]23[C@]14[C@H](O4)C(C3)(C)C)O

Technology Process of Alliacol A

There total 38 articles about Alliacol 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: 88.0%

(+/-)-12-noralliacolide (79232-31-8,122743-34-4,122743-35-5) → (+/-)-alliacol A (79232-29-4,122743-30-0,122743-37-7)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; 1.) -20 to 0 deg C, 1.5 h, 2.) -20 deg C to r.t., 12 h;

DOI:10.1021/jo00120a027

Reference yield: 45.0%

eschenmoser's salt (33797-51-2) + (+/-)-12-noralliacolide (79232-31-8,122743-34-4,122743-35-5) → (+/-)-alliacol A (79232-29-4,122743-30-0,122743-37-7)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -20 - 25 ℃; for 12h;

DOI:10.1016/S0040-4039(00)82176-0

Reference yield:

cyclopent-2-enone (930-30-3) → (+/-)-alliacol A (79232-29-4,122743-30-0,122743-37-7)

Guidance literature:

Multi-step reaction with 22 steps

1: 77 percent / n-BuLi / 1.) THF, hexane, 20 deg C, 1 h; HMPA, -78 deg C, 30 min, 2.) -78 deg C, 24 h; 0 deg C, 1 h

2: 94 percent / 10percent HCl / tetrahydrofuran / 4 h / Heating

3: 1.) CuI / 1.) ether, THF, 0 deg C, 45 min, 2.) 0 deg C, 3 h

4: 96 percent / LDA / 1.) THF, cyclohexane, -78 deg C, 2 h; -20 deg C, 18 h, 2.) HMPA, -78 deg C, 30 min; -78 deg C, 4 h

5: 99 percent / L-Selectride / tetrahydrofuran / 3 h

6: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, r.t., 1.2 h, 2.) 20 min

7: 96 percent / 70percent HClO₄ / benzene; CCl₄ / 1.) 0 deg C, 15 min, 2.) 30 min

8: 85percent m-CPBA, NaHCO₃ / CH₂Cl₂ / 3 h / 0 °C

9: aq. KOH / CH₂Cl₂; methanol / 1 h / Ambient temperature

10: 96 percent / p-TsOH*H₂O / benzene / 1.5 h / Heating

11: aq. K₂CO₃ / methanol / 48 h / Ambient temperature

12: 95 percent / LDA / 1.) THF, cyclohexane, -78 deg C to r.t., 3 h, 2.) HMPA, -78 deg C, 1 h

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -55 deg C, 30 min, 2.) -55 deg C, 1 h; -55 to 0 deg C, 1 h

14: 98 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C

15: 48 percent / DIBAL-H / toluene; hexane / 1.5 h / -78 °C

16: LiAlH₄ / diethyl ether / 3.5 h / Ambient temperature

17: 98 percent / pyridine, DMAP / CH₂Cl₂ / 0.5 h

18: 88 percent / aq. KOH, BHT / tetrahydrofuran / 0.25 h / 0 °C

19: 89 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 1.) -78 deg C, 2 h, 2.) r.t., 42 h

20: 98 percent / 80percent m-CPBA, Na₂CO₃ / CH₂Cl₂ / 2 h

21: 98 percent / aq. NaIO₄, aq. Na₂CO₃, aq. RuCl₃ / CCl₄; acetonitrile / 96 h / Ambient temperature

22: 88 percent / LiTMP / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.) -20 to 0 deg C, 1.5 h, 2.) -20 deg C to r.t., 12 h

With pyridine; hydrogenchloride; dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium methylate; trimethoxonium tetrafluoroborate; L-Selectride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;

DOI:10.1021/jo00120a027

upstream raw materials:

(3aR,9aS)-3a-Hydroxy-6,8,8-trimethyl-3-methylene-3a,4,5,6,8,9-hexahydro-3H-indeno[3a,4-b]furan-2-one

(1RS,7RS)-2,3,4,5,6,7-Hexahydro-1-hydroxy-2,2,7-trimethyl-1H-inden-4-one

Methanesulfonic acid (1R,7R)-2,2,7-trimethyl-4-oxo-2,3,4,5,6,7-hexahydro-1H-inden-1-yl ester

(1RS,7RS)-1-Acetoxy-2,3,4,5,6,7-hexahydro-2,2,7-trimethyl-1H-inden-4-one

Downstream raw materials:

(+/-)-alliacolide

Refernces

• 1、 Clair, James J. La,Landsbury, Peter T.,Zhi, Ben-xin,Hoogsteen, Karst. "A Stereoselective Total Synthesis of (+/-)-Alliacol A and Congeners of Marasmius Alliaceus". . p. 4822 - 4833. Retrieved 2007/10/02.