(3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione

Base Information

Chemical Name:(3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione
CAS No.:6754-14-9
Molecular Formula:C15H18O3
Molecular Weight:246.3
Hs Code.:
DSSTox Substance ID:DTXSID601110862
Nikkaji Number:J20.608C
Wikidata:Q105199261
Mol file:6754-14-9.mol

Synonyms:DTXSID601110862;(3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione

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

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Chemical Property of (3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione

Chemical Property:

Melting Point:159-160 °C(Solv: acetone (67-64-1); hexane (110-54-3))
Boiling Point:418.5±45.0 °C(Predicted)
Density:1.16±0.1 g/cm3(Predicted)
XLogP3:2.4
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:0
Exact Mass:246.125594432
Heavy Atom Count:18
Complexity:476

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1CC2C(CC3(C1C=CC3=O)C)C(=C)C(=O)O2
Isomeric SMILES:C[C@@H]1C[C@@H]2[C@H](C[C@]3([C@H]1C=CC3=O)C)C(=C)C(=O)O2

Technology Process of (3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione

There total 17 articles about (3aR,4aS,7aR,8R,9aR)-3,3a,4,4a,7a,8,9,9a-Octahydro-4a,8-dimethyl-3-methyleneazuleno[6,5-b]furan-2,5-dione 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: 78.0%

: (+/-)-(3aR*,4aS*,7aS*,8R*,9aS*)-3a,4,4a,5,6,7,7a,8,9,9a-decahydro-6-(phenylselenyl)-4a,8-dimethyl-3-methyleneazuleno<6,5-b>furan-2(3H)-one

: 5945-42-6,6754-14-9,74645-41-3,74645-43-5
(+/-)-aromaticin

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; for 16h; Ambient temperature;
DOI:10.1021/jo00057a012

Reference yield:

: 123130-59-6
3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one

: 5945-42-6,6754-14-9,74645-41-3,74645-43-5
(+/-)-aromaticin

Guidance literature:: Multi-step reaction with 11 steps

1: 77 percent / EtAlCl₂ / toluene / 1 h / Ambient temperature

2: 83 percent / Me₂AlCl / CH₂Cl₂; hexane / 3 h / Ambient temperature

3: 1.) Li, liqu. NH₃ / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 3 h

4: 1.) diborane, 2.) 3 N NaOH, 30 percent H₂O₂ / 1.a) THF, -78 deg C, 4 h, b) -50 deg C, 2 h, c) 0 deg C, 10 h, 2.) 45 deg C, 2 h

5: 3 percent / O₂ / PtO₂ / H₂O; acetone / 8 h / 50 °C

6: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -25 deg C

7: 60 percent / pyridine / 10 h / Ambient temperature

8: 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 10 h / Ambient temperature

9: 86 percent / pyridinium dichromate / CH₂Cl₂ / 10 h / Ambient temperature

10: 91 percent / HCl / ethyl acetate / 10 h / Ambient temperature

11: 78 percent / NaIO₄ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium periodate; dipyridinium dichromate; ammonia; dihydrogen peroxide; oxygen; dimethylaluminum chloride; ethylaluminum dichloride; lithium; diborane; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene;
DOI:10.1021/jo00057a012

Reference yield:

: (+/-)-(3R*,3aS*,5R*,6S*,8R*)-1,6-dihydroxy-3a,8-dimethyl-1,2,3,3a,4,5,6,7,8,8a-decahydroazulene-5-ethanol

: 5945-42-6,6754-14-9,74645-41-3,74645-43-5
(+/-)-aromaticin

Guidance literature:: Multi-step reaction with 7 steps

1: 3 percent / O₂ / PtO₂ / H₂O; acetone / 8 h / 50 °C

2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -25 deg C

3: 60 percent / pyridine / 10 h / Ambient temperature

4: 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 10 h / Ambient temperature

5: 86 percent / pyridinium dichromate / CH₂Cl₂ / 10 h / Ambient temperature

6: 91 percent / HCl / ethyl acetate / 10 h / Ambient temperature

7: 78 percent / NaIO₄ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium periodate; dipyridinium dichromate; oxygen; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00057a012