Betaenone B

Base Information

• Chemical Name: Betaenone B
• CAS No.: 85269-23-4
• Molecular Formula: C₂₁H₃₆O₅
• Molecular Weight: 368.514
• NSC Number: 376691
• UNII: C9873620HS
• DSSTox Substance ID: DTXSID40234463
• Nikkaji Number: J91.878D
• Wikipedia: Betaenone_B
• Wikidata: Q4897328
• Metabolomics Workbench ID: 144106
• Mol file: 85269-23-4.mol

Synonyms:BETAENONE B;85269-23-4;UNII-C9873620HS;C9873620HS;1(2H)-Naphthalenone, octahydro-2,7-dihydroxy-4-(3-hydroxy-1-oxopropyl)-2,4,5,7-tetramethyl-3-((1R)-1-methylpropyl)-, (2S,3R,4R,4aS,5R,7R,8aS)-;NSC376691;SCHEMBL11136602;DTXSID40234463;CHEBI:145054;NSC-376691;Q4897328;(2S,3R,4R,4AS,5R,7R,8AS)-3-SEC-BUTYL-2,7-DIHYDROXY-4-(3-HYDROXYPROPANOYL)-2,4,5,7-TETRAMETHYLOCTAHYDRONAPHTHALEN-1(2H)-ONE

Chemical Property of Betaenone B

Chemical Property:

• Vapor Pressure: 7.41E-13mmHg at 25°C
• Boiling Point: 517.1°Cat760mmHg
• Flash Point: 280.6°C
• PSA: 94.83000
• Density: 1.09g/cm³
• LogP: 2.35350
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 368.25627424
• Heavy Atom Count: 26
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C1C(C2C(CC(CC2C(=O)C1(C)O)(C)O)C)(C)C(=O)CCO
• Isomeric SMILES: CC[C@@H](C)[C@@H]1[C@]([C@H]2[C@@H](C[C@@](C[C@@H]2C(=O)[C@@]1(C)O)(C)O)C)(C)C(=O)CCO

Technology Process of Betaenone B

There total 22 articles about Betaenone B 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: 34.0%

(2S,3R,4R,4aS,5R,7R,8aS)-3-((R)-sec-Butyl)-2,7-dihydroxy-4-(3-methoxy-propionyl)-2,4,5,7-tetramethyl-octahydro-naphthalen-1-one → betaenone B (85269-23-4)

Guidance literature:

With aluminium trichloride; ethanethiol; at -8 ℃; for 4h;

DOI:10.1016/S0040-4039(01)80742-5

Reference yield:

Nerol (106-25-2) → betaenone B (85269-23-4)

Guidance literature:

Multi-step reaction with 19 steps

1: Sharpless oxidation

3: 60 percent / imidazole / dimethylformamide / Ambient temperature

4: LDA / tetrahydrofuran / -40 °C

5: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -50 °C

6: pyridine / 36 h / Ambient temperature

7: Pr₂NEt / 24 h / Ambient temperature

8: n-Bu₄NF / tetrahydrofuran / 3.5 h / 0 °C

9: n-Bu₃P / pyridine / 24 h / Ambient temperature

10: 99.7 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 14 h / -20 - -10 °C

12: SiO₂ / benzene / 36 h / Ambient temperature

13: oxalyl chloride / dimethylsulfoxide / 0.33 h / -55 °C

14: 46.8 percent / BuLi / 40 h / -4 - -3 °C

15: 40.5 percent / toluene / 36 h / 115 °C / sealed tube

16: 66.1 percent / OsO₄ / pyridine; diethyl ether / 3 h / -30 °C

17: 65.3 percent / PCC, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

18: 91.7 percent / AlCl₃, NaI / acetonitrile; CH₂Cl₂ / 30 h / 20 °C

19: 34 percent / AlCl₃, EtSH / 4 h / -8 °C

With 1H-imidazole; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; dipropylethylamine; tributylphosphine; tetrabutyl ammonium fluoride; sodium acetate; silica gel; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; ethanethiol; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(01)80742-5

Reference yield:

(2E, 4R)-2,4-dimethyl-2-hexen-1-ol (127760-69-4) → betaenone B (85269-23-4)

Guidance literature:

Multi-step reaction with 10 steps

1: PCC / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3: SiO₂ / benzene / 36 h / Ambient temperature

4: oxalyl chloride / dimethylsulfoxide / 0.33 h / -55 °C

5: 46.8 percent / BuLi / 40 h / -4 - -3 °C

6: 40.5 percent / toluene / 36 h / 115 °C / sealed tube

7: 66.1 percent / OsO₄ / pyridine; diethyl ether / 3 h / -30 °C

8: 65.3 percent / PCC, NaOAc / CH₂Cl₂ / 1 h / Ambient temperature

9: 91.7 percent / AlCl₃, NaI / acetonitrile; CH₂Cl₂ / 30 h / 20 °C

10: 34 percent / AlCl₃, EtSH / 4 h / -8 °C

With osmium(VIII) oxide; n-butyllithium; aluminium trichloride; oxalyl dichloride; sodium acetate; silica gel; pyridinium chlorochromate; ethanethiol; sodium iodide; In pyridine; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(01)80742-5

upstream raw materials:

Nerol

(2E, 4R)-2,4-dimethyl-2-hexen-1-ol

(-)-2-Methylbutan-1-ol

(2R,4R)-6-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-hexane-1,4-diol

Downstream raw materials:

betaenone F

(-)-betaenone C

betaenone A

Refernces

• 1、 Ichihara, Akitami,Miki, Shokyo,Kawagishi, Hirokazu,Sakamura, Sadao. "TOTAL SYNTHESIS OF (-)-BETAENONE C". . p. 4551 - 4554. Retrieved 2007/10/02.