(+/-)-1-epi-alliacolide

Base Information

• Chemical Name: (+/-)-1-epi-alliacolide
• CAS No.: 101834-24-6
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 101834-24-6.mol

Synonyms:

Chemical Property of (+/-)-1-epi-alliacolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-1-epi-alliacolide

There total 60 articles about (+/-)-1-epi-alliacolide 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: 90.0%

(+/-)-alliacol A (79232-29-4,122743-30-0,122743-37-7) → (+/-)-alliacolide (66389-08-0,101834-24-6,120663-95-8,122743-31-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h; under 1551.4 Torr;

DOI:10.1021/jo00120a027

Reference yield:

cyclopent-2-enone (930-30-3) → (+/-)-alliacolide (66389-08-0,101834-24-6,120663-95-8,122743-31-1)

Guidance literature:

Multi-step reaction with 23 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

23: 90 percent / H₂ / 10percent Pd/C / methanol / 2 h / 1551.4 Torr

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; hydrogen; 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; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;

DOI:10.1021/jo00120a027

Reference yield:

1,2,3,3a,5,6-Hexahydro-4,4-(1,3-propanediyldithio)-4H-inden-1-one (167101-24-8) → (+/-)-alliacolide (66389-08-0,101834-24-6,120663-95-8,122743-31-1)

Guidance literature:

Multi-step reaction with 21 steps

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

2: 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

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

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

5: 96 percent / 70percent HClO₄ / benzene; CCl₄ / 1.) 0 deg C, 15 min, 2.) 30 min

6: 85percent m-CPBA, NaHCO₃ / CH₂Cl₂ / 3 h / 0 °C

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

8: 96 percent / p-TsOH*H₂O / benzene / 1.5 h / Heating

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

10: 95 percent / LDA / 1.) THF, cyclohexane, -78 deg C to r.t., 3 h, 2.) HMPA, -78 deg C, 1 h

11: 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

12: 98 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / 0 °C

13: 48 percent / DIBAL-H / toluene; hexane / 1.5 h / -78 °C

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

15: 98 percent / pyridine, DMAP / CH₂Cl₂ / 0.5 h

16: 88 percent / aq. KOH, BHT / tetrahydrofuran / 0.25 h / 0 °C

17: 89 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 1.) -78 deg C, 2 h, 2.) r.t., 42 h

18: 98 percent / 80percent m-CPBA, Na₂CO₃ / CH₂Cl₂ / 2 h

19: 98 percent / aq. NaIO₄, aq. Na₂CO₃, aq. RuCl₃ / CCl₄; acetonitrile / 96 h / Ambient temperature

20: 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

21: 90 percent / H₂ / 10percent Pd/C / methanol / 2 h / 1551.4 Torr

With pyridine; dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; copper(l) iodide; lithium aluminium tetrahydride; perchloric acid; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; 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; palladium on activated charcoal; 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:

(+/-)-12-noralliacolide

(+/-)-8,9-deoxyalliacolide

(+/-)-alliacol A

4-Hydroxy-6-(3-iodo-1-methyl-propyl)-3,8,8-trimethyl-1-oxa-spiro[4.4]nona-3,6-dien-2-one