38419-75-9

Basic information

• Product Name: 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)-
• CAS NO: 38419-75-9
• Molecular Weight: 254.413
• Mol File: 38419-75-9.mol
• Article Data: 44

Chemical Properties

• CAS DataBase Reference: 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- (CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- (38419-75-9)
• EPA Substance Registry System: 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- (38419-75-9)

Safety Data

• Hazardous Substances Data: 38419-75-9(Hazardous Substances Data)

Usage

General Description

1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- is a complex chemical compound that falls under the category of steroids. It is a naturally occurring substance with a unique molecular structure that consists of naphthalene, ethanol, and various hydroxyl and methyl groups. 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- is a chiral molecule, meaning it has a non-superimposable mirror image, and its stereochemistry is denoted by the (1R,2R,4aS,8aS) designation. 1-Naphthaleneethanol,decahydro-2-hydroxy- 2,5,5,8a-tetramethyl-,(1R,2R,4aS,8aS)- has diverse applications in medicinal chemistry, organic synthesis, and biochemistry, and it is important for further understanding and research in chemical and biological sciences.

Upstream product

• 564-20-5 (3aR)-(+)-sclareolide 
• 186790-39-6 12-bromosclareol oxide 
• 106672-01-9 (1R,2R,8aS)-2,5,5,8a-tetramethyl-1-(2-oxoethyl)decahydronaphthalen-2-yl acetate 
• 564-20-5 trans-syn-cis norambreinolide 
• 564-20-5 norisoambreinolide 
• 247905-32-4 2-[(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-yl]-ethanol 
• 64061-39-8 (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 
• 515-03-7 sclareol 
• 105014-29-7 8α-hydroxy-13,14,15,16-tetranorlabdan-12-al 
• 138171-15-0 8-acetoxy-labdanolic acid 
• 145511-17-7 15-nor-8-acetoxy-13-labdene 
• 145511-24-6 15-nor-8-acetoxy-12-labdene 
• 469-11-4 labdanolic acid 
• 145511-19-9 15-nor-8-hydroxy-12-labdene 

Downstream Products

• 3738-00-9 (±)-ambrox 
• 38419-77-1 (4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene 
• 3738-00-9 (3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 
• 3738-00-9 (+/-)-5β-Ambrox 
• 10207-83-7 (+/-)-13,14,15,16-Tetranor-5β-labdane-8α,12-diol 
• 1395881-48-7 C₂₃H₃₄O 
• 72853-81-7 Aureol 
• 1395881-53-4 C₂₃H₃₀N₂O₆ 
• 1395881-46-5 C₂₂H₃₁NO₂Se 
• 1424348-29-7 Δ^8,13-bicyclohomofarnezenic acid N-(pyrimidin-2-yl)amide 
• 1424348-23-1 2-bis-Δ^8,13-bicyclohomofarnezenoylaminopyrimidine 
• 1424348-25-3 N-Δ^8,13-bicyclohomofarnezenoyl-N,N′-dicyclohexylurea 
• 1424348-20-8 Δ^8,13-bicyclohomofarnezenic acid N-(pyrimidin-4-yl)amide 
• 1424348-28-6 Δ^8,13-bicyclohomofarnezenic acid N-(pyrazinil-3-yl)amide 

Relevant articles and documents

Transformations of sclareol oxide by bromination. Synthesis of driman-8α, 11-diol from sclareol oxide

Depending on reaction conditions, the reaction of sclareol oxide with N-bromosuccinimide affords either 12-bromo-or 12,16-dibromosclareol oxide, whereas the reaction of sclareol oxide with bromine in methanol gives 12-monobromide or (13S)-11,12-dibromo-8α

Practical synthesis of Ambrox from farnesyl acetate involving lipase catalyzed resolution

Enantiomerically pure Ambrox was synthesized from (-)-13,14,15,16- tetranor-8α,12-labdanediol, which was prepared by lipase catalyzed kinetic resolution of (±)-drimane-8,11-diol.

An Efficient Synthesis of Wiedendiol-A from (+)-Sclareolide

An efficient synthesis of Wiedendiol-A (1) is described starting from commercially available (+)-sclareolide.This synthesis also confirms the absolute stereochemistry of Wiedendiol-A.

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Total synthesis of (-)-thallusin: Utilization of enzymatic hydrolysis resolution

Thallusin, isolated from a marine bacterium, is the only known natural product to act as an algal morphogenesis inducer. Because (-)-thallusin can only be obtained in exceedingly limited amounts from microbial cultivation, a synthetic supply of this compound is highly desirable. Here, we describe a novel synthetic pathway to (±)-thallusin and the first asymmetric synthesis of (-)-thallusin utilizing the enzymatic hydrolysis resolution with the combination of lipase PS-30 and lipase M Amamo-10.

The synthesis of (-)-Ambrox starting from labdanolic acid

Iododecarboxylation of labdanolic acid (1), followed by dehydrohalogenation led to alkenes 4 and 12. Both compounds were converted into (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydro-2- naphthalenol (8), which was transformed via cyclization into (-)-Ambrox (9).

Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol

The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.

MANGANESE-CATALYSED HYDROGENATION OF ESTERS

The present invention relates to the field of catalytic hydrogenation and, more particularly, to methods of manganese-catalysed hydrogenation of esters to alcohols. Advantageously, where the esters are chiral, the hydrogenations proceed with high or complete stereochemical integrity..

USE OF A RUTHENIUM CATALYST COMPRISING A TETRADENTATE LIGAND FOR HYDROGENATION OF ESTERS AND/OR FORMATION OF ESTERS AND A RUTHENIUM COMPLEX COMPRISING SAID TETRADENTATE LIGAND

The present invention relates to the use of a transition metal catalyst TMC1, which comprises a transition metal M selected from metals of groups 7, 8, 9 and 10 of the periodic table of elements according to IUPAC and a tetradentate ligand of formula I wherein R1 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, and R2 are identical or different and are each an organic radical having from 1 to 40 carbon atoms, as catalyst in processes for formation of compounds comprising at least one carboxylic acid ester functional group -O-C(=O)- starting from at least one primary alcohol and/or hydrogenation of compounds comprising at least one carboxylic acid ester functional group -O-C(=O)-. The present invention further relates to a process for hydrogenation of a compound comprising at least one carboxylic acid ester functional group -O-C(=O)-, to a process for the formation of a compound comprising at least one carboxylic acid ester functional group -O-C(=O)- by dehydrogenase coupling of at least one primary alcohol with a second alcoholic OH-group, to a transition metal complex comprising the tetradentate ligand of formula I and to a process for preparing said transition metal complex.