Hispanolone

Base Information

• Chemical Name: Hispanolone
• CAS No.: 18676-07-8
• Molecular Formula: C20H30O3
• Molecular Weight: 318.4504
• NSC Number: 332876
• DSSTox Substance ID: DTXSID00420022
• Nikkaji Number: J16.132B
• Wikidata: Q82231273
• Metabolomics Workbench ID: 126053
• ChEMBL ID: CHEMBL2000054
• Mol file: 18676-07-8.mol

Synonyms:hispanolone

Chemical Property of Hispanolone

Chemical Property:

• Vapor Pressure: 1.05E-07mmHg at 25°C
• Boiling Point: 417.2°Cat760mmHg
• Flash Point: 206.1°C
• PSA: 50.44000
• Density: 1.045g/cm³
• LogP: 4.38480
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 472

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)CC2C(CCCC2(C1(CCC3=COC=C3)O)C)(C)C
• Isomeric SMILES: C[C@@H]1C(=O)C[C@@H]2[C@@]([C@]1(CCC3=COC=C3)O)(CCCC2(C)C)C

Technology Process of Hispanolone

There total 23 articles about Hispanolone 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: 79.0%

(+)-(2S,3R,4S,4aS,8aS)-3,4-epoxy-4-[2-(3-furyl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-3,4a,8,8-tetramethylnaphth-2-ol (82509-26-0) → (-)-Hispanolone (18676-07-8)

Guidance literature:

(+)-(2S,3R,4S,4aS,8aS)-3,4-epoxy-4-[2-(3-furyl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-3,4a,8,8-tetramethylnaphth-2-ol; With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h;

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)00627-4

Reference yield:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → (-)-Hispanolone (18676-07-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: diisopropylamine; n-Buli / tetrahydrofuran; hexane / 0.75 h / 0 °C

1.2: 83 percent / tetrahydrofuran; hexane / 0.83 h / 20 °C

2.1: 94 percent / benzyltrimethylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

3.1: 97 percent / pyridinium bromide perbromide / acetic acid / 2 h / 20 °C

4.1: 94 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating

5.1: 99 percent / diethyl ether / -78 - 20 °C

6.1: 98 percent / N,N-dimethylaminopyridine / tetrahydrofuran / 21 h / 20 °C

7.1: 80 percent / Pd(PPh₃)4; CuI / diethylamine / 12 h / Heating

8.1: 98 percent / n-Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

9.1: 78 percent / pyridinium chlorochromate / CH₂Cl₂ / 58 h / 20 °C

10.1: 85 percent / H₂; aq. KOH / Pd/C / methanol / 0.12 h

11.1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.08 h / 0 °C

12.1: 92 percent / imidazole / dimethylformamide / 0 - 20 °C

13.1: 70 percent Turnov_. / NaHCO₃; m-chloroperoxybenzoic acid / CH₂Cl₂ / 12 h / 0 °C

14.1: 88 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

15.1: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

15.2: 79 percent / pyridinium dichromate / CH₂Cl₂ / 0.75 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; pyridinium hydrobromide perbromide; trimethyl(benzyl)ammonium fluoride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; diethylamine; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: silylation / 2.1: Methylation / 3.1: Bromination / 4.1: Dehydrobromination / 5.1: Addition / 6.1: Substitution / 7.1: Substitution / 8.1: desilylation / 9.1: Oxidation / 10.1: Catalytic hydrogenation / 11.1: Reduction / 12.1: Substitution / 13.1: Epoxidation / 14.1: desilylation / 15.1: Reduction / 15.2: Oxidation;

DOI:10.1016/S0040-4020(99)00627-4

Reference yield:

(-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one (25487-94-9,823785-67-7) → (-)-Hispanolone (18676-07-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 99 percent / diethyl ether / -78 - 20 °C

2.1: 98 percent / N,N-dimethylaminopyridine / tetrahydrofuran / 21 h / 20 °C

3.1: 80 percent / Pd(PPh₃)4; CuI / diethylamine / 12 h / Heating

4.1: 98 percent / n-Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

5.1: 78 percent / pyridinium chlorochromate / CH₂Cl₂ / 58 h / 20 °C

6.1: 85 percent / H₂; aq. KOH / Pd/C / methanol / 0.12 h

7.1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.08 h / 0 °C

8.1: 92 percent / imidazole / dimethylformamide / 0 - 20 °C

9.1: 70 percent Turnov_. / NaHCO₃; m-chloroperoxybenzoic acid / CH₂Cl₂ / 12 h / 0 °C

10.1: 88 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

11.1: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

11.2: 79 percent / pyridinium dichromate / CH₂Cl₂ / 0.75 h / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; diethylamine; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Substitution / 3.1: Substitution / 4.1: desilylation / 5.1: Oxidation / 6.1: Catalytic hydrogenation / 7.1: Reduction / 8.1: Substitution / 9.1: Epoxidation / 10.1: desilylation / 11.1: Reduction / 11.2: Oxidation;

DOI:10.1016/S0040-4020(99)00627-4

upstream raw materials:

(-)-Prehispanolone

7β-hispanol

(+)-(2S,3R,4S,4aS,8aS)-3,4-epoxy-4-[2-(3-furyl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-3,4a,8,8-tetramethylnaphth-2-ol

(+)-(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethylnaphthalen-1-ol

Downstream raw materials:

(+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one

6α-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one

6β-hydroxy-15,16-epoxy-labda-8,13(16),14-trien-7-one

Refernces

• 1、 Cheung, Wing Shun,Wong, Henry N. C.. "Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone". . p. 11001 - 11016. Retrieved 2007/10/03.