Chaparrinone

Base Information

• Chemical Name: Chaparrinone
• CAS No.: 22611-34-3
• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.422
• Nikkaji Number: J34.227K
• Wikidata: Q27106141
• NCI Thesaurus Code: C1046
• Metabolomics Workbench ID: 67903
• ChEMBL ID: CHEMBL472016
• Mol file: 22611-34-3.mol

Synonyms:chaparrinone

Chemical Property of Chaparrinone

Chemical Property:

• Vapor Pressure: 2.67E-18mmHg at 25°C
• Melting Point: 238-242 °C
• Boiling Point: 626.1°Cat760mmHg
• PKA: 12.03±0.70(Predicted)
• Flash Point: 224.9°C
• PSA: 113.29000
• Density: 1.45g/cm³
• LogP: 0.16620
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 378.16785316
• Heavy Atom Count: 27
• Complexity: 776

Purity/Quality:

98%,99%, ^*data from raw suppliers

CHAPARRINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2CC(=O)OC3C24COC(C1O)(C4C5(C(C3)C(=CC(=O)C5O)C)C)O
• Isomeric SMILES: C[C@@H]1[C@@H]2CC(=O)O[C@H]3[C@@]24CO[C@@]([C@@H]1O)([C@@H]4[C@@]5([C@@H](C3)C(=CC(=O)[C@H]5O)C)C)O

Technology Process of Chaparrinone

There total 46 articles about Chaparrinone 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: 67.0%

(+)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxypicras-3-ene-2,11,16-trione (149400-26-0) → chaparrinone (22611-34-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/ja00067a025

Reference yield:

(E)-4-methyl-3,5-hexadienoic acid (95421-98-0) → (+/-)-chaparrinone (22611-34-3,130575-31-4,138752-52-0)

Guidance literature:

Multi-step reaction with 24 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

20: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF

21: 1.) HCl, 2.) PCC, NaOAc / 1.) H₂O, THF, 2.) CH₂Cl₂

22: 1.) PyHBr₃, CSA, 2.) LiBr, Li₂CO₃ / 1.) THF, 1 h, 2.) DMF, 120 deg C, 1 h

23: BBr₃ / CH₂Cl₂ / 1.5 h / -78 - -23 °C

24: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; boron tribromide; lithium; lithium carbonate; diisobutylaluminium hydride; sodium carbonate; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

Reference yield:

(4aR,5S,8S,8aR)-8-Methoxy-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde (86669-09-2,87758-23-4,123929-85-1) → (+/-)-chaparrinone (22611-34-3,130575-31-4,138752-52-0)

Guidance literature:

Multi-step reaction with 24 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

20: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF

21: 1.) HCl, 2.) PCC, NaOAc / 1.) H₂O, THF, 2.) CH₂Cl₂

22: 1.) PyHBr₃, CSA, 2.) LiBr, Li₂CO₃ / 1.) THF, 1 h, 2.) DMF, 120 deg C, 1 h

23: BBr₃ / CH₂Cl₂ / 1.5 h / -78 - -23 °C

24: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; boron tribromide; lithium; lithium carbonate; diisobutylaluminium hydride; sodium carbonate; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

upstream raw materials:

ailanthone

(+)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxypicras-3-ene-2,11,16-trione

(+)-(1β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicras-11-ene

(-)-(1β)-20-(tert-butyldiphenylsiloxy)-1-hydroxypicras-11-en-16-one

Downstream raw materials:

Acetic acid (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-2,11-diacetoxy-3,8,11a-trimethyl-1,5,10-trioxo-1,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-2H-6-oxa-benzo[de]anthracen-11c-ylmethyl ester