68365-88-8

Basic information

• Product Name: (5aα,9bα)-3aα,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan
• Synonyms: (3aS,5aα,9bα)-Dodecahydro-3aα,6,6,9aβ-tetramethylnaphtho[2,1-b]furan;(5aα,9bα)-3aα,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan;Isoambrox;(3aR,5aR,9bS)-3aβ,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan;(-)-9-Epiambrox;(-)-9-epi-Ambrox;(3aR,5aα,9bβ)-Dodecahydro-3a,6,6,9aβ-tetramethylnaphtho[2,1-b]furan;[3aR,5aα,9bβ,(-)]-Dodecahydro-3aβ,6,6,9aβ-tetramethylnaphtho[2,1-b]furan
• CAS NO: 68365-88-8
• Molecular Formula: C₁₆H₂₈O
• Molecular Weight: 236.39292
• Mol File: 68365-88-8.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5aα,9bα)-3aα,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan(CAS DataBase Reference)
• NIST Chemistry Reference: (5aα,9bα)-3aα,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan(68365-88-8)
• EPA Substance Registry System: (5aα,9bα)-3aα,6,6,9aβ-Tetramethyldodecahydronaphtho[2,1-b]furan(68365-88-8)

Safety Data

• Hazardous Substances Data: 68365-88-8(Hazardous Substances Data)

Upstream product

• 110202-07-8 (E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 110202-08-9 (Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol 
• 459-89-2 (3E,7E)-homofarnesol 
• 138152-06-4 (3Z,7E)-4,8,12-Trimethyltrideca-3,7,11-trien-1-ol 
• 564-20-5 trans-syn-cis norambreinolide 
• 35826-67-6 homofarnesol 
• 38419-75-9 (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol 
• 158577-90-3 <1S-(1α,2β,3β,4β,4aβ,8aα)> decahydro-3-hydroxyl-2,5,5,8a-tetramethylnaphthalene-1-ethanol 
• 99733-97-8 3-methyl-5-(2',6',6'-trimethylcyclohex-1'-enyl)-1-penten-3-ol 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 133859-01-5 (E)-4-Methyl-6-(2',2'-dimethyl-6'-methylidenecyclohexyl)hex-3-en-1-ol 
• 133858-86-3 (E)-4-Methyl-6-(2',6',6'-trimethyl-2'-cyclohexenyl)hex-3-en-1-ol 
• 138152-07-5 (3E,7Z)-4,8,12-Trimethyltrideca-3,7,11-trien-1-ol 
• 133859-02-6 (Z)-4-Methyl-6-(2',2'-dimethyl-6'-methylidenecyclohexyl)hex-3-en-1-ol 

Downstream Products

• 3738-00-9 (3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 
• 3738-00-9 (-)-norlabdane 
• 122566-19-2 <3aR-(3aα,4α,6aα,10aS^*)> dodecahydro-3a,4,7,7-tetramethyl-2H-naphtho<8a,1-b>furan 

Relevant articles and documents

Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction

The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid-mediated cationic cyclisation reaction is disclosed. This high-yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen-containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9-epi-Ambrox demonstrates the potential of the reaction for natural product synthesis.

Diastereoselective Synthesis of (±)-Ambrox by Titanium(III)-Catalyzed Radical Tandem Cyclization

A synthesis of (±)-ambrox, a compound with delicious ambergris-type scent, is presented. The key step is a highly diastereoselective titanocene(III)-catalyzed radical tandem cyclization of a farnesol derivative.

Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate

The reaction of 1,4-diols with dimethyl carbonate in the presence of a base led to selective and high-yielding syntheses of related five-membered cyclic ethers. This synthetic pathway has the potential for a wide range of applications. Distinctive cyclic ethers and industrially relevant compounds were synthesized in quantitative yield. The reaction mechanism for the cyclization was investigated. Notably, the chirality of the starting material was maintained. DFT calculations indicated that the formation of five-membered cyclic ethers was energetically the most favorable pathway. Typically, the selectivity exhibited by these systems could be rationalized on the basis of hard-soft acid-base theory. Such principles were applicable as far as computed energy barriers were concerned, but in practice cyclization reactions were shown to be entropically driven. Copyright