pentalenolactone E

Base Information

Chemical Name:pentalenolactone E
CAS No.:72715-03-8
Molecular Formula:C₁₅H₁₈O₄
Molecular Weight:262.306
Hs Code.:
DSSTox Substance ID:DTXSID701107541
Nikkaji Number:J12.626H
Wikidata:Q27139111
Metabolomics Workbench ID:65274

Synonyms:pentalenolactone E;(4aR,7aS,9aR)-6,6-dimethyl-4-methylene-3-oxo-1,3,4,5,6,7,7a,9a-octahydropentaleno[1,6a-c]pyran-9-carboxylic acid;72715-03-8;CHEBI:70807;DTXSID701107541;C20398;Q27139111;(4aR,6aS,9aR)-8,8-dimethyl-1-methylidene-2-oxo-4a,6a,7,9-tetrahydro-4H-pentaleno[1,6a-c]pyran-5-carboxylic acid

Suppliers and Price of pentalenolactone E

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

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Total 0 raw suppliers

Chemical Property of pentalenolactone E

Chemical Property:

PSA：63.60000
LogP:2.16280
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:262.12050905
Heavy Atom Count:19
Complexity:528

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1(CC2C=C(C3C2(C1)C(=C)C(=O)OC3)C(=O)O)C
Isomeric SMILES:CC1(C[C@H]2C=C([C@H]3[C@]2(C1)C(=C)C(=O)OC3)C(=O)O)C

Technology Process of pentalenolactone E

There total 15 articles about pentalenolactone E 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:

: 89111-51-3
3-pentalenen-6-ol

: 72715-03-8,89163-60-0
pentalenolactone E

Guidance literature:: Multi-step reaction with 11 steps

1: 71 percent / hydroboration-oxidation

2: 87 percent / 15 h / 85 °C

3: 86 percent / SeO₂ / ethanol / 24 h / Heating

4: NaCN/MnO₂/AcOH / room temp., 18 h

5: 78 percent / 0 °C / Jones oxidation

6: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

7: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

8: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

9: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

10: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

11: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;
DOI:10.1016/S0040-4039(00)94293-X

Reference yield:

: 89111-52-4,89163-66-6
(1R,2R,3aR,4S,5aR,8aS)-1,4,7,7-Tetramethyl-octahydro-cyclopenta[c]pentalene-2,3a-diol

: 72715-03-8,89163-60-0
pentalenolactone E

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / 15 h / 85 °C

2: 86 percent / SeO₂ / ethanol / 24 h / Heating

3: NaCN/MnO₂/AcOH / room temp., 18 h

4: 78 percent / 0 °C / Jones oxidation

5: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

6: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

7: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

8: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

9: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

10: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;
DOI:10.1016/S0040-4039(00)94293-X

Reference yield:

: 80786-92-1,89163-64-4
(Z)-(3aR,4R,9aR)-4-Methoxy-2,2,4,8-tetramethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacyclooctene

: 72715-03-8,89163-60-0
pentalenolactone E

Guidance literature:: Multi-step reaction with 13 steps

1: 1.) hydroboration-oxidation; 2.) Jones oxidation

2: 1.) formic acid; 2.) sodium carbonate / 1.) 45 grad C, 2h: 2.) methanol-water, room temp., 6h

3: 71 percent / hydroboration-oxidation

4: 87 percent / 15 h / 85 °C

5: 86 percent / SeO₂ / ethanol / 24 h / Heating

6: NaCN/MnO₂/AcOH / room temp., 18 h

7: 78 percent / 0 °C / Jones oxidation

8: 1.) TMSOTf, Et₃N; 2.) NBS / 1.) benzene, room temp., 10 min; 2.) THF, 5 min

9: 30 percent / Et₃N, NaHCO₃ / benzene / 24 h / Ambient temperature

10: 80 percent / (TMS)2NH / benzene / 2 h / Ambient temperature

11: 1.) mCPBA; 2.) NaIO₄ / 1.) hexane, - 15 deg C, 30 min; room temp., 2h; 2.) H₂O-t-BuOH, room temp., 4h

12: 1.) NaBH₄; 2.) 2N HCl / 1.) EtOH, 0 degC, 10 min; 2.) pH 2, room temp., 2 h

13: 1.) LiOH; 2.) 1N HCl / 1.) H₂O-THF, room temp.; 2.) pH 2, room temp., 2 h

With hydrogenchloride; manganese(IV) oxide; lithium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; formic acid; selenium(IV) oxide; trimethylsilyl trifluoromethanesulfonate; sodium cyanide; sodium hydrogencarbonate; sodium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethanol; benzene;
DOI:10.1016/S0040-4039(00)94293-X