1-benzylperhydrohistrionicotoxin

Base Information

Chemical Name:1-benzylperhydrohistrionicotoxin
CAS No.:119203-94-0
Molecular Formula:C₂₆H₄₃NO
Molecular Weight:385.634
Hs Code.:

Synonyms:

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Chemical Property of 1-benzylperhydrohistrionicotoxin

Chemical Property:

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Technology Process of 1-benzylperhydrohistrionicotoxin

There total 38 articles about 1-benzylperhydrohistrionicotoxin 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:

: 32362-97-3
2-pentylcyclohexanone

: 119203-94-0,122675-02-9
1-benzyl-2,6-epiperhydrohistrionicotoxin

Guidance literature:: Multi-step reaction with 19 steps

1: 71 percent / hydroxylamine-O-sulfonic acid, formic acid / 1 h / Heating

2: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h

3: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

5: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

6: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

7: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

8: 59 percent / toluene / 40 h / 110 °C

9: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

10: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

11: Dibal / diethyl ether; toluene / 6 h / -78 °C

12: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

13: 4 M HCl / 3 h

14: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

15: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

16: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

17: NaBH₄ / methanol / 0.5 h / 0 °C

18: 58 percent / AlCl₃, LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

19: 1.) BH₃/Me₂S, 2.) H₂O₂, 10percent NaOH / 1.) THF, 40 deg C, 24 h, 2.) diglyme, 80 deg C, 14 h

With Lawessons reagent; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; formic acid; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide; borane; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; hydroxylamine-O-sulfonic acid; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/jo00279a034

Reference yield:

: 32362-97-3
2-pentylcyclohexanone

: 119203-94-0,122675-02-9
1-benzylperhydrohistrionicotoxin

Guidance literature:: Multi-step reaction with 19 steps

1: 71 percent / hydroxylamine-O-sulfonic acid, formic acid / 1 h / Heating

2: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h

3: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

5: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

6: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

7: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

8: 59 percent / toluene / 40 h / 110 °C

9: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

10: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

11: Dibal / diethyl ether; toluene / 6 h / -78 °C

12: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

13: 4 M HCl / 3 h

14: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

15: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

16: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

17: NaBH₄ / methanol / 0.5 h / 0 °C

18: 58 percent / AlCl₃, LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

19: 1.) BH₃/Me₂S, 2.) H₂O₂, 10percent NaOH / 1.) THF, 40 deg C, 24 h, 2.) diglyme, 80 deg C, 14 h

With Lawessons reagent; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; formic acid; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide; borane; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; hydroxylamine-O-sulfonic acid; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/jo00279a034

Reference yield:

: 84460-49-1
7-pentylhexahydroazepin-2-one

: 119203-94-0,122675-02-9
1-benzylperhydrohistrionicotoxin

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h

2: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

4: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

5: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

6: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

7: 59 percent / toluene / 40 h / 110 °C

8: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

9: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

10: Dibal / diethyl ether; toluene / 6 h / -78 °C

11: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

12: 4 M HCl / 3 h

13: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

14: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

15: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

16: NaBH₄ / methanol / 0.5 h / 0 °C

17: 58 percent / AlCl₃, LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

18: 1.) BH₃/Me₂S, 2.) H₂O₂, 10percent NaOH / 1.) THF, 40 deg C, 24 h, 2.) diglyme, 80 deg C, 14 h

With Lawessons reagent; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; Phenylselenyl chloride; oxalyl dichloride; dimethylsulfide; borane; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/jo00279a034