(-)-Neoavarone

Base Information

• Chemical Name: (-)-Neoavarone
• CAS No.: 129445-46-1
• Molecular Formula: C21H28O2
• Molecular Weight: 312.452
• Mol file: 129445-46-1.mol

Synonyms:

Chemical Property of (-)-Neoavarone

Chemical Property:

• PSA: 34.14000
• LogP: 4.80970

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-Neoavarone

There total 23 articles about (-)-Neoavarone 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: 73.0%

(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene → Arenarone (87764-16-7,106190-06-1,129445-46-1)

Guidance literature:

With ammonium cerium(IV) nitrate; sodium hydrogencarbonate; In Dimethyl ether; acetonitrile; for 43.2h; Ambient temperature;

DOI:10.1021/jo00121a030

Reference yield: 57.0%

(-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene (184485-50-5) → 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione (129445-46-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; for 5h; Ambient temperature;

DOI:10.1021/jo962292l

Reference yield:

o-Methoxybenzyl bromide (52289-93-7) → 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione (129445-46-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / Li; liq. NH₃ / tetrahydrofuran

2: 86 percent / t-BuOK / benzene / Heating

3: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

4: 80 percent / H₂; Et₃N / 10 percent Pd/C / methanol / 20 °C / 760 Torr

5: 100 percent / t-BuOK / benzene / Heating

6: 92 percent / n-BuSLi / hexamethylphosphoric acid triamide / 4 h / 100 °C

7: 91 percent / O₂ / N,N-bis(salicylidene)ethylenediiminocobalt(II) / dimethylformamide / 7 h / 20 °C

With hydrogenchloride; potassium tert-butylate; ammonia; hydrogen; oxygen; lithium; lithium-n-butanethiolate; triethylamine; palladium on activated charcoal; salcomine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol

(-)-(1R,4aS,8aS)-1β,2β,4aβ-trimethyl-1α-[(2',5'-dimethoxyphenyl)methyl]-5-exo-methylene-(3H)-1,4,4a,5,6,7,8,8a-octahydronaphthalene

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

o-Methoxybenzyl bromide

Downstream raw materials:

(+/-)-Arenarol

2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol

Refernces

• 1、 Radeke,Digits,Bruner,Snapper. "New tools for studying vesicular-mediated protein trafficking: Synthesis and evaluation of ilimaquinone analogs in a non-radioisotope-based antisecretory assay". . p. 2823 - 2831. Retrieved 2007/10/03.
• 2、 Iguchi,Sahashi,Kohno,Yamada. "New sesquiterpenoid hydroquinone and quinones from the Okinawan marine sponge (Dysidea sp.)". . p. 1121 - 1123. Retrieved 2007/10/02.