AMBROX DL

Base Information

• Chemical Name: AMBROX DL
• CAS No.: 3738-00-9
• Deprecated CAS: 21582-36-5,193980-58-4,193980-58-4
• Molecular Formula: C16H28 O
• Molecular Weight: 236.398
• Hs Code.: 2932999099
• European Community (EC) Number: 223-118-6
• DSSTox Substance ID: DTXSID2048119
• Nikkaji Number: J205.641K
• Wikidata: Q81976567
• Metabolomics Workbench ID: 47525
• ChEMBL ID: CHEMBL3728760
• Mol file: 3738-00-9.mol

Synonyms:3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan;Amberlyn; Ambrox DL; Cetalox; Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan;Synambran

Chemical Property of AMBROX DL

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: 75-85ºC
• Boiling Point: 273.9 ºC at 760 mmHg
• Flash Point: 104.8 ºC
• PSA: 9.23000
• Density: 0.939 g/cm³
• LogP: 4.40800
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 236.214015512
• Heavy Atom Count: 17
• Complexity: 322

Purity/Quality:

99.9% ^*data from raw suppliers

DODECAHYDRO-3ALPHA,6,6,9ALPHA-TETRAMETHYL-NAPHTHO[2,1-B]FURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CCO3)C)C)C

Technology Process of AMBROX DL

There total 237 articles about AMBROX DL 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: 100.0%

(d,l)-13,14,15,16-tetranor-8α,12-epoxy-2-labdene → (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1021/jo980211a

Reference yield: 75.0%

(Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol (110202-08-9) → (3aRS,5aRS,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (3aR,5aR,9aR,9bR)-3a,6,6,9a-Tetramethyl-dodecahydro-naphtho[2,1-b]furan + (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With chlorosulfonic acid; 1-Nitropropane; at -78 ℃; for 0.15h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo951908o

Reference yield: 75.0%

(Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol (110202-08-9) → (3aRS,5aRS,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (3aR,5aR,9aR,9bR)-3a,6,6,9a-Tetramethyl-dodecahydro-naphtho[2,1-b]furan + (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With chlorosulfonic acid; 1-Nitropropane; at -78 ℃; for 0.15h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo951908o

upstream raw materials:

(3Z,7E)-4,8,12-Trimethyltrideca-3,7,11-trien-1-ol

(3E,7E)-homofarnesol

(Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol

(E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol

Downstream raw materials:

(3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan

(-)-norlabdane

<3aR-(3aα,4α,6aα,10aS^*)> dodecahydro-3a,4,7,7-tetramethyl-2H-naphtho<8a,1-b>furan

Refernces

• 1、 Rosales, Antonio,Foley,Padial, Natalia M.,Muoz-Bascn, Juan,Sancho-Sanz, Iris,Roldan-Molina, Esther,Pozo-Morales, Laura,Iras-lvarez, Adriana,Rodrguez-Maecker, Roman,Rodrguez-Garca, Ignacio,Oltra, J. Enrique. "Diastereoselective Synthesis of (±)-Ambrox by Titanium(III)-Catalyzed Radical Tandem Cyclization". . p. 369 - 374. Retrieved 2016/02/09.
• 2、 Aricó, Fabio,Tundo, Pietro,Maranzana, Andrea,Tonachini, Glauco. "Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate". experimental part. p. 1578 - 1586. Retrieved 2012/10/07.