(4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol

Base Information

• Chemical Name: (4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol
• CAS No.: 5173-70-6
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.306
• European Community (EC) Number: 225-957-3
• DSSTox Substance ID: DTXSID101184385
• Nikkaji Number: J294.559B
• Mol file: 5173-70-6.mol

Synonyms:5173-70-6;SCHEMBL6005394;DTXSID101184385;EINECS 225-957-3;4alpha,8abeta-Dimethyloctahydronaphthalen-4abeta(8aH)-ol;(4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol;4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4alpha,4abeta,8abeta)-

Chemical Property of (4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol

Chemical Property:

• Boiling Point: 252.4°Cat760mmHg
• Flash Point: 104.2°C
• Density: 0.985g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 182.167065321
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC2(C1(CCCC2)O)C
• Isomeric SMILES: C[C@H]1CCC[C@@]2([C@]1(CCCC2)O)C

Technology Process of (4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol

There total 18 articles about (4alpha,4Abeta,8abeta)-octahydro-4,8a-dimethyl-4a(2H)-naphthol 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: 81.0%

1,4a-dimethyl-trans-3,4,4a,5,6,7,8,8a-otahydronaphthalen-8a-ol (73428-93-0,132087-77-5) → r-1,c-4a-dimethylperhydronaphthalen-t-8a-ol (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; at 100 ℃; for 36h; under 72200.1 Torr;

Reference yield: 72.0%

Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester (125107-10-0,125137-16-8) → (+/-)-Geosmin (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1016/S0040-4039(00)99122-6

Reference yield:

(+/-)-perhydro-7β,8aβ-dihydroxy-1β-methylnaphthalene-4aα-carbaldehyde (126370-56-7) → (+/-)-Geosmin (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Py*TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1) N₂H₄; 2) KOH; 3) Py*TsOH / 1) 110 deg C, 30 min; 2) 180 deg C, 1 h; 3) MeOH, 60 deg C, 30 min

3: 90 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

4: Zn powder, NaI / 1,2-dimethoxy-ethane / 4 h / 90 - 95 °C

With pyridine; potassium hydroxide; pyridinium p-toluenesulfonate; sodium iodide; hydrazine; zinc; pyridinium p-toluenesulfonate; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1002/hlca.19900730114

upstream raw materials:

trans-8,10-Dimethyl-1⁽⁹⁾-octalin

Methanesulfonic acid (2S,4aR,8R,8aR)-8a-hydroxy-4a,8-dimethyl-decahydro-naphthalen-2-yl ester

1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one

Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester

Downstream raw materials:

markiertes 8ref,10cis-Dimethyl-1(9)-octalin

Refernces

• 1、 Hansson, Lars,Carlson, Rolf. "Synthesis of (+/-)-Geosmin. Part 2. A One-Pot Four-Step Conversion of 1,4a-Dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one into (+/-)-Geosmin". . p. 1042 - 1045. Retrieved 2007/10/02.
• 2、 Ayer,Browne,Fung. "Metabolites of bird's nest fungi. Part VI. The synthesis of (±)cybullol and a new synthesis of (±)geosmin". . p. 3276 - 3282. Retrieved 2007/10/11.