823785-65-5

Basic information

• Product Name: 1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI)
• Synonyms: 1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI)
• CAS NO: 823785-65-5
• Molecular Formula: C14H24O
• Molecular Weight: 208.33976
• Product Categories: METHYL
• Mol File: 823785-65-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI)(823785-65-5)
• EPA Substance Registry System: 1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI)(823785-65-5)

Safety Data

• Hazardous Substances Data: 823785-65-5(Hazardous Substances Data)

Usage

Uses

Used in Perfumery Industry:
1(2H)-Naphthalenone,octahydro-2,5,5,8a-tetramethyl-,(4aR,8aS)-rel-(9CI) is used as a fragrance ingredient for its musk-like odor, providing a sweet and powdery scent to perfumes, lotions, and other scented products.
Used in Cosmetics and Personal Care Products:
Isoambrettolide is used as a substitute for musk deer musk in the production of cosmetics and personal care products, offering a long-lasting and safe alternative to the endangered animal product.

Upstream product

• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 113666-03-8 (4aS,6S,8aS)-5,5,8a-trimethyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 224048-20-8 Methyl (2ζ,4aS,8aS)-decahydro-5,5,8a-trimethyl-1-oxonaphthalene-2-carboxylate 
• 138812-34-7 (R)-6-methylcarvone 
• 110188-61-9 (5S,6S)-6-(2-bromoallyl)-5-isopropenyl-2,6-dimethyl-2-cyclohexen-1-one 
• 224048-24-2 (2ζ,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 79886-54-7 11-nordrimane-8α,9β-diol 
• 110188-66-4 (2R)-2-hydroxy-11-nordrim-7-en-9-one 
• 25487-94-9 (-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one 
• 20404-64-2 drimenol 
• 74-88-4 methyl iodide 
• 224048-16-2 O-<(4aS,8aS)-5,5-Ethylenedioxydecahydro-1,1,4a-trimethylnaphthalen-2-yl> S-methyl dithiocarbonate 
• 91547-54-5 (4aS,8aS)-3,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one ethylene acetal 

Downstream Products

• 20404-65-3 (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 82462-67-7 (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one 
• 25487-94-9 (-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one 

Relevant articles and documents

High-Pressure Approach to the Total Synthesis of (+/-)-Ambreinolide and (+/-)-8-Epiambreinolide

Ambreinolide (7a) and its epimer (7b) have been synthesized regioselectively and in a stereocontrolled manner from (+/-)-trans-1,1,4aβ-trimethyldecahydronaphthalen-5-one (1) by a route (Scheme I) which relies upon the promotion of a key Diels-Alder reaction under conditions of high pressure.

A total synthesis of (±)-hispanolone

Hispanolone (1), employed recently in our partial synthesis of the specific platelet activating factor antagonist prehispanolone (2), was prepared from (±)-Wieland-Miescher ketone (4).

Concise syntheses of (+)-austrodoral and (+)-austrodoric acid Based on H2O2 mediated oxidative ring contraction

Asymmetric synthesis of the marine nor-sesquiterpenoid (+)-austrodoric acid and (+)-austrodoral in seven and nine steps respectively from Wieland-Miescher ketone was described herein. The synthesis featured an oxidative ring contraction of α-formyl cyclic ketone mediated by H2O2 to forge the hydrindane scaffold together with the contiguous quaternary carbon centers simultaneously.

Divergent Synthesis of Marine Natural Products Siphonodictyal B, Corallidictyals C/D, and Liphagal Based on the Early Presence of an Aldehyde Group Instead of a Late-Stage Introduction

An iodine-promoted sunlight-induced olefin Z/E isomerization reaction together with a palladium-catalyzed direct cross-coupling reaction of a drimanal hydrazone and an iodobenzaldehyde, without touching the aromatic aldehyde group, facilitated a divergent and expeditious access to bioactive marine natural products siphonodictyal B, corallidictyals C/D, and liphagal based on the early presence of an aldehyde group instead of a late-stage introduction.

Regiodivergent Remote Arylation of Cycloalkanols to Dysideanone′s Fused Carbotetracycles and Its Bridged Isomers

Regiodivergent γ and γ′ arylations across an all-carbon quaternary center of cycloalkanols to access enantioenriched fused and bridged carbotetracycles are reported. The conformation of the carbocation guided either sequential stereospecific β-C-Me/γ-C?H-shifts or β-C-Me/γ′-C?H-shifts, providing fused carbotetracyclic analogs of dysideanone or bridged tetracycles, respectively. The reaction is highly stereoselective in building three contiguous stereocenters, where one, two, or three could be all-carbon quaternary centers. Interestingly, mechanistic studies revealed a crucial role of a methyl substituent in controlling regioselectivity.

Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

Synthetic method of austrodoral and austrodoric acid

The invention relates to a synthetic method of an ocean terpene natural product austrodoral, austordoric acid and a land terpene natural product 8-epi-11-nordriman-9-one and belongs to the field of chemical synthesis. Sesquiterpenes vicinal diol is prepared by selective ozonization reaction of sesquiterpenes enol, the land terpene natural product 8-epi-11-nordriman-9-one and the ocean terpene natural product austrodoral are synthesized by the selective rearrangement reaction of the sesquiterpenes vicinal diol, and the ocean terpene natural product austrodoric acid is synthesized by oxidation reaction of the austrodoral. The method has the characteristics of low production cost, simple process conditions, easiness in control, suitability for industrial production, high overall yield and the like.

Biomimetic Enantioselective Total Synthesis of (?)-Mycoleptodiscin A

Biomimetic total synthesis of (?)-mycoleptodiscin A (1) was achieved starting from the enantiopure key intermediate, which was prepared by Friedel-Crafts reaction between 7-methoxyindole and chiral primary allylic alcohol. The crucial step in this synthes

Enantioselective access to (-)-Ambrox starting from β-farnesene

Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t

Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against drosophila melanogaster til-til

Natural compounds from Drimys winteri Forst and derivatives exhibited larvicidal effects against Drosophila melanogaster til-til. The most active compound was isodrimenin (4). The highest lethal concentration to the larvae of D. melanogaster was 4.5 ± 0.8 mg/L. At very low concentrations drimenol (1), confertifolin (3), and drimanol (5) displayed antifeedant and larvae growth regulatory activity. The antifeedant results of nordrimanic and drimanic compounds were better in first instar larvae. The EC50 value of polygodial (2) was 60.0 ± 4.2 mg/L; of diol 15 45.0 ± 2.8 mg/L, and of diol 17 36.9 ± 3.7 mg/L, while the new nordrimane compound 12 presented a value of 83.2 ± 3.5 mg/L.