(1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde

Base Information

• Chemical Name: (1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde
• CAS No.: 3243-36-5
• Molecular Formula: C16H26O
• Molecular Weight: 234.382
• Mol file: 3243-36-5.mol

Synonyms:1-Naphthaleneacetaldehyde,decahydro-5,5,8a-trimethyl-2-methylene- (6CI,7CI,8CI);1-Naphthaleneacetaldehyde, decahydro-5,5,8a-trimethyl-2-methylene-, [1S-(1a,4ab,8aa)]-;13,14,15,16-Tetranorlabd 8(17)-en-12-al;Ambrial;g-Bicyclohomofarnesal;

Chemical Property of (1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde

Chemical Property:

• Boiling Point: 307.329 °C at 760 mmHg
• Flash Point: 144.917 °C
• PSA: 17.07000
• Density: 0.941 g/cm³
• LogP: 4.37420

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ambergris is a synthetic fragrance that has been found in almost all fragrances since its discovery. It is now like the salt and pepper necessary for cooking, and it is the most successful member of the synthetic flavor.
• Description: Ambergris ketone, which can be named octahydrotetramethylnaphthyl ethyl ketone according to scientific nomenclature, was first discovered by IFF researchers JohnB.Hall and JamesMlookchem.Sanders in the process of studying violet odor compounds. Initially they named it IsocyclemoneE, and later, after improving the synthesis method, the resulting product was renamed IsoESuper?.

Technology Process of (1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde

There total 4 articles about (1S,4aS,8aS)-Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde 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:

(+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) → (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde (3243-36-5)

Guidance literature:

Multi-step reaction with 4 steps

1: KMnO₄; MgSO₄ / acetone / 20 °C

2: 66 percent / oxygen / 1,2-dimethoxy-ethane / 4 h / 20 °C

3: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4: 8 percent / molecular sieves 4 Angstroem; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂

With potassium permanganate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; oxygen; magnesium sulfate; 4-methylmorpholine N-oxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; acetone;

DOI:10.1080/00397910500377172

Reference yield:

manool (596-85-0,1438-62-6,29461-42-5,41357-91-9,106631-38-3) → (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde (3243-36-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 5 g / t-butyl hydroperoxide, vanadyl acetylacetonate / benzene

2: 4.7 g / LiAlH₄ / diethyl ether / 1 h / Heating

3: 3.5 g / sodium periodate / H₂O; methanol / Ambient temperature

4: 3.2 g / sodium hypobromite / dioxane

5: 0.57 g / LDA, diperoxo(oxohexamethylphosphoramido)molybdenum(VI) / tetrahydrofuran; hexane / 2 h / -5 °C

6: 0.6 g / LiAlH₄ / diethyl ether / 1 h / Heating

7: 0.1 g / sodium periodate / H₂O; methanol / Ambient temperature

With tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; sodium hypobromide; diperoxo(oxohexamethylphosphoramido)molybdenum(VI); vanadyl acetylacetonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; water; benzene;

DOI:10.1071/CH9880711

Reference yield:

(1R,2R,4aS,8aS)-(+)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene (64061-39-8) → 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetaldehyde (116163-52-1,88862-14-0) + (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde (3243-36-5)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

upstream raw materials:

(1R,2R,4aS,8aS)-(+)-1-(2'-acetoxyethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthalene

8α-acetoxy-13,14,15,16-tetranor-12-labdanoic acid

(+)-manool

manool

Downstream raw materials:

5S,9S,10S-(-)-(E)-labda-8⁽¹⁷⁾,11,13-trien-16,15-olide

3-((1S)-1-hydroxy-2-((1 S,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)-furan-2(5H)-one

3-[(1R)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-1-hydroxyethyl]-2,5-dihydrofuran-2-one

galanolactone

Refernces

• 1、 Villamizar, Jose,Fuentes, Juan,Salazar, Franklin,Tropper, Eleonora,Alonso, Randolph. "Facile Access to Optically Active Labdane-Type Diterpenes from (+)-Manool. Synthesis of (+)-Coronarin E, (+)-15,16-Epoxy-8(17),13(16),14-labdatriene, and (+)-Labda-8(17),13(Z)-diene-15,16-diol". . p. 1623 - 1627. Retrieved 2007/10/03.
• 2、 Cambie, Richard C.,Moratti, Stephen C.,Rutledge, Peter S.,Weston, Roderick J.,Woodgate, Paul D.. "A Synthesis of (-)-12,15-Epoxylabda-8(17),12,14-trien-16-yl Acetate and (-)-Pumiloxide". . p. 1151 - 1162. Retrieved 2007/10/02.