481656-25-1

Basic information

• Product Name: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one
• Synonyms: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one
• CAS NO: 481656-25-1
• Molecular Weight: 314.468
• Mol File: 481656-25-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one(481656-25-1)
• EPA Substance Registry System: (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one(481656-25-1)

Safety Data

• Hazardous Substances Data: 481656-25-1(Hazardous Substances Data)

Upstream product

• 481656-23-9 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one 
• 481656-21-7 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one-5-ethyleneacetal 
• 481656-19-3 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal 
• 52289-93-7 o-Methoxybenzyl bromide 
• 26742-33-6 (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal 

Downstream Products

• 481656-15-9 (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-5-(methylene)decahydronaphthalene 
• 129445-46-1 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione 
• 129443-87-4 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)decahydronaphthalen-1-yl]methyl]benzene-1,4-diol 
• 544423-12-3 2-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-(methylene)-decahydronaphthalen-1-yl]methyl]phenol 
• 481656-12-6 (1R,2S,4aS,5R,6S,8aS)-2-[(5β,6β-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol 
• 481656-13-7 (1R,2S,4aS,5S,6R,8aS)-2-[(5α,6α-epoxy-1β,2β,4aβ,5α-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)-methyl]phenol 
• 481656-29-5 (1R,2S,4aS,8aR)-2-[(1β,2β,4aβ,5-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-1-yl)methyl]phenol 
• 481656-27-3 (1S,2S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ,5-tetramethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene 

Relevant articles and documents

Enantioselective total synthesis of (+)-stachyflin: A potential anti-influenza a virus agent isolated from a microorganism

A novel and potent hemagglutinin inhibitor, (+)-stachyflin, was efficiently synthesized in an enantioselective manner starting from the (+)-5-methyl-Wieland-Miescher ketone. The synthetic method features a BF 3·Et2O-induced cascade epoxide-opening/ rearrangement/cyclization reaction tostereoselectively construct the requisite pentacyclic ring system in one step. In order to rationalize the mechanism of the cascade reaction, quantum chemical calculations of the possible intermediary carbocations and transition states in the model synthesis were carried out. An alternative approach to synthesize (+)-stachyflin by employing a similar cascade reaction was also described. A potential anti-influenza A virus agent, (+)-stachyflin, a novel hemagglutinin inhibitor, has been synthesized in an enantioselective manner for the first time starting from (+)-5-methyl-Wieland- Miescher ketone. The method features a BF3·Et 2O-induced cascade epoxide-opening/rearrangement/cyclization reaction to construct the requisite pentacyclic ring system in one step.

Highly Improved Synthesis of (+)-Aureol via (-)-Neoavarone and (-)-Neoavarol, by Employing Salcomine Oxidation and Acid-Induced Rearrangement/Cyclization Strategy

A short and efficient synthesis of (+)-aureol (1), a structurally novel and biologicaly important marine natural product, was achieved starting with readily available (+)-Wieland-Miescher ketone analogue 7 via (-)-neoavarone (10) and (-)-neoavarol (11). The method features salcomine oxidation of the phenol derivative 9 to deliver 10 and BF3*OEt2-induced rearrangement/cyclization reaction of 11 to produce 1 as the crucial steps. The improvement biomimetic synthesis required only 9 steps and proceeds in 31 percent overall yield.