20404-65-3

Basic information

• Product Name: (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one
• Synonyms: (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one
• CAS NO: 20404-65-3
• Molecular Weight: 208.344
• Mol File: 20404-65-3.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one(20404-65-3)
• EPA Substance Registry System: (-)-(2R,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one(20404-65-3)

Safety Data

• Hazardous Substances Data: 20404-65-3(Hazardous Substances Data)

Upstream product

• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 138812-34-7 (R)-6-methylcarvone 
• 78835-25-3 2,4,5-Trimethoxy-3-[(2S,8aS)-2,5,5,8a-tetramethyl-octahydro-naphthalen-(1E)-ylidenemethyl]-benzaldehyde 
• 20404-64-2 drimenol 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 
• 74-88-4 methyl iodide 
• 1376654-78-2 C₁₆H₂₆O₂ 
• 1376654-31-7 (1R,2R,4aS,8aS)-1-(iodoethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl formate 
• 103476-92-2 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol 
• 79886-54-7 11-nordrimane-8α,9β-diol 
• 86546-84-1 (5S,8R,10S)-drim-9⁽¹¹⁾-en-8-ol 
• 468-68-8 (-)-drimenol 
• 91547-50-1 (4aS,8aS)-5,5,8a-trimethylhexahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6(5H)-one 
• 41722-49-0 (S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione 

Downstream Products

• 1259067-32-7 C₂₂H₃₁BrO₃ 
• 1259067-33-8 C₂₂H₃₂O₃ 
• 1259067-34-9 C₂₂H₃₂O₃ 
• 905291-19-2 C₂₆H₄₁BrO₄Si 
• 905291-20-5 C₂₃H₃₃BrO₄ 
• 224048-12-8 (-)-(1'S,2'S,2R)-4-(2'-Hydroxy-2',6',6'-trimethylcyclohexyl)-2-methylbutanoic acid 
• 6790-58-5 (-)-ambroxide 
• 564-20-5 (3aR)-(+)-sclareolide 
• 1227311-31-0 C₄₀H₅₂O₂ 
• 1227311-20-7 C₃₇H₅₆O₂Si 

Relevant articles and documents

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.

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.