(+/-)-aromaticin

Base Information

• Chemical Name: (+/-)-aromaticin
• CAS No.: 74645-43-5
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 74645-43-5.mol

Synonyms:

Chemical Property of (+/-)-aromaticin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-aromaticin

There total 17 articles about (+/-)-aromaticin 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 → (+/-)-aromaticin (5945-42-6,6754-14-9,74645-41-3,74645-43-5)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; for 16h; Ambient temperature;

DOI:10.1021/jo00057a012

Reference yield:

3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one (123130-59-6) → (+/-)-aromaticin (5945-42-6,6754-14-9,74645-41-3,74645-43-5)

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

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

upstream raw materials:

(3aS,4aR,5R,7aR,8S,9aR)-5-tert-Butoxy-4a,8-dimethyl-3-methylene-decahydro-azuleno[6,5-b]furan-2-one

3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one

2,3-dihydroaromaticin

(+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one