Graveolide

Base Information

• Chemical Name: Graveolide
• CAS No.: 72173-44-5
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 72173-44-5.mol

Synonyms:2,3-dihydroaromaticin;2,3‐dihydroaromaticin;(3aR,4aS,7aS,8R,9aS)-4a,8-Dimethyl-3-methylene-decahydro-azuleno[6,5-b]furan-2,5-dione;

Chemical Property of Graveolide

Chemical Property:

• Boiling Point: 407.3±45.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 2.49950

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Graveolide

There total 18 articles about Graveolide 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: 86.0%

(+/-)-(3aR*,4aS*,5R*,7aS*,8R*,9aS*)-3a,4,4a,5,6,7,7a,8,9,9a-decahydro-4a,8-dimethyl-5-hydroxy-3-methyleneazuleno<6,5-b>furan-2(3H)-one → 2,3-dihydroaromaticin (6605-59-0,19908-69-1,19908-81-7,60426-81-5,72173-44-5,74645-40-2,74645-42-4,110115-60-1,50334-39-9)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/jo00057a012

Reference yield:

3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one (123130-59-6) → 2,3-dihydroaromaticin (6605-59-0,19908-69-1,19908-81-7,60426-81-5,72173-44-5,74645-40-2,74645-42-4,110115-60-1,50334-39-9)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; sodium hydroxide; 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 hexane; dichloromethane; water; 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 → 2,3-dihydroaromaticin (6605-59-0,19908-69-1,19908-81-7,60426-81-5,72173-44-5,74645-40-2,74645-42-4,110115-60-1,50334-39-9)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dipyridinium dichromate; oxygen; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; platinum(IV) oxide; In dichloromethane; water; 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

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

(+/-)-4-methyl-1,2,3,4,5,8-hexahydro-1-oxoazulene-7-ethanol

Downstream raw materials:

(+/-)-aromaticin

Refernces

• 1、 Lansbury, Peter T.,Hangauer, David G.,Vacca, Joseph P.. "Total Synthesis of Pseudoguaianolides: (+/-)-Aromaticin and (+/-)-Aromatin". . p. 3964 - 3965. Retrieved 2007/10/02.