((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate

Base Information

• Chemical Name: ((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate
• CAS No.: 193410-84-3
• Molecular Formula: C21H18O7
• Molecular Weight: 382.37
• DSSTox Substance ID: DTXSID90441923
• Nikkaji Number: J852.475K
• Wikidata: Q72516831
• ChEMBL ID: CHEMBL4468212
• Mol file: 193410-84-3.mol

Synonyms:zeylenone

Chemical Property of ((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate

Chemical Property:

• Melting Point: 150-152℃
• PSA: 110.13000
• Density: 1.41
• LogP: 1.29990
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 382.10525291
• Heavy Atom Count: 28
• Complexity: 616

Purity/Quality:

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

Zeylenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2(C(C(C=CC2=O)OC(=O)C3=CC=CC=C3)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@]2([C@H]([C@@H](C=CC2=O)OC(=O)C3=CC=CC=C3)O)O
• Description: Zeylenone, isolated from the ethanolic extract of the leaves of Uvaria grandiflora Roxb.
• Uses: Zeylenone is mainly used for content determination.

Technology Process of ((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate

There total 16 articles about ((1S,5R,6S)-5-(Benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)methyl benzoate 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: 100.0%

((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate (78804-17-8) → (-)-Tonkinenin A (193410-84-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; ethyl acetate;

DOI:10.1039/a905631i

Reference yield:

benzoyl chloride (98-88-4) → (-)-Tonkinenin A (193410-84-3)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine; DMAP

2: NMO; OsO₄; H₂O / tetrahydrofuran / 20 °C

3: Zn; NH₄Cl; H₂O / tetrahydrofuran / Heating

4: dimethylformamide / 80 °C

5: Ph₂O / 0.25 h / Heating

6: HF / acetonitrile

7: 100 percent / MnO₂ / CH₂Cl₂; ethyl acetate

With pyridine; dmap; manganese(IV) oxide; osmium(VIII) oxide; N-methyl-2-indolinone; diphenylether; hydrogen fluoride; water; ammonium chloride; zinc; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Oxidation / 3: Ring cleavage / 4: Substitution / 5: Elimination / 6: Desilylation / 7: Oxidation;

DOI:10.1039/a905631i

Reference yield:

(+)-(1R,4S,4aR,5S,8aS)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one (194796-30-0) → (-)-Tonkinenin A (193410-84-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 89 percent / NaH / tetrahydrofuran / 20 °C

2: 82 percent / O₂; KF; (EtO)3P / dimethylsulfoxide

3: NaBH₄ / methanol; tetrahydrofuran / -15 °C

4: NBS / CH₂Cl₂ / -15 °C

5: 84 percent / POCl₃; pyridine / 50 °C

6: DIBAL-H / toluene / -78 °C

7: Bu₄NF / tetrahydrofuran / 20 °C

8: pyridine; DMAP

9: NMO; OsO₄; H₂O / tetrahydrofuran / 20 °C

10: Zn; NH₄Cl; H₂O / tetrahydrofuran / Heating

11: dimethylformamide / 80 °C

12: Ph₂O / 0.25 h / Heating

13: HF / acetonitrile

14: 100 percent / MnO₂ / CH₂Cl₂; ethyl acetate

With pyridine; dmap; manganese(IV) oxide; potassium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; diphenylether; hydrogen fluoride; tetrabutyl ammonium fluoride; water; oxygen; sodium hydride; diisobutylaluminium hydride; ammonium chloride; zinc; triethyl phosphite; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Condensation / 2: Oxidation / 3: Reduction / 4: Bromination / 5: Dehydration / 6: Reduction / 7: desilylation / 8: Acylation / 9: Oxidation / 10: Ring cleavage / 11: Substitution / 12: Elimination / 13: Desilylation / 14: Oxidation;

DOI:10.1039/a905631i

upstream raw materials:

((1R,2S,5R,6S)-5-(benzoyloxy)-1,2,6-trihydroxycyclohex-3-en-1-yl)methyl benzoate

(-)-Uvarigranol G

benzoyl chloride

(+)-(1R,4S,4aR,5S,8aS)-5-tert-Butyldimethylsilyloxy-1,4,4a,6,7,8-hexahydro-endo-1,4-methanonaphthalen-8(5H)-one

Downstream raw materials:

(-)-Uvarigranol G

2-O-acetylzeylenone

(1R,2R,3S)-2-acetyl-zeylenone

Refernces

• 1、 Takeuchi,Cheng,Shi,Sugiyama,Oritani. "Four polyoxygenated cyclohexenes from the Chinese tree, Uvaria purpurea.". . p. 1395 - 1398. Retrieved 2001.