81002-19-9

Basic information

• Product Name: (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate
• Synonyms: (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate
• CAS NO: 81002-19-9
• Molecular Weight: 300.441
• Mol File: 81002-19-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate(81002-19-9)
• EPA Substance Registry System: (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (E)-but-2-enoate(81002-19-9)

Safety Data

• Hazardous Substances Data: 81002-19-9(Hazardous Substances Data)

Upstream product

• 625-35-4 trans-chrotonyl chloride 
• 65253-04-5 (-)-8-phenylmenthol 
• 100-58-3 phenylmagnesium bromide 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 205057-17-6 (5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanone 
• 89-82-7 pulegone 
• 1330630-28-8 C₂₀H₂₈O₂ 
• 81002-20-2 (+)-8-phenylmenthyl Z-crotonate 
• 107-93-7 (E)-but-2-enoic acid 

Downstream Products

• 81002-23-5 (S)-3-Methyl-heptanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 65253-04-5 (-)-8-phenylmenthol 
• 81002-21-3 (E)-Hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 81002-20-2 (+)-8-phenylmenthyl Z-crotonate 
• 169136-81-6 (-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate 
• 1330630-29-9 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (S,S)-3-[N-benzyl-N-(α-methylbenzyl)amino]butanoate 
• 1330630-38-0 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (S)-3-(N-isopropyl-N-benzylamino)butanoate 
• 1330630-43-7 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (R)-3-(N-isopropyl-N-benzylamino)butanoate 
• 1330630-33-5 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (R,R)-3-[N-benzyl-N-(α-methylbenzyl)amino]butanoate 
• 1330630-37-9 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (S)-3-(N,N-dibenzylamino)butanoate 
• 1330630-42-6 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (R)-3-(N,N-dibenzylamino)butanoate 
• 1330630-47-1 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (S)-3-aminobutanoate 
• 1330630-49-3 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (R)-3-aminobutanoate 
• 1330630-55-1 (1'R,2'S,5'R)-2'-(2''-phenylpropan-2''-yl)-5'-methylcyclohexyl (R)-3-(N-isopropylamino)butanoate 

Relevant articles and documents

Double asymmetric induction as a mechanistic probe: The doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α,β-unsaturated esters and enantiopure α,β-unsaturated hydroxamates

The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure α,β-unsaturated esters [derived from Corey's 8-phenylmenthol chiral auxiliary] and enantiopure α,β-unsaturated hydroxamates [derived from our 'chiral Weinreb amide' auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxylamine] has been used as a mechanistic probe to determine the reactive conformations of these acceptors.

THE RACEMIC FORM AND THE TWO ENANTIOMERS OF 4-METHYL-1-NONANOL, A SEX ATTRACTANT OF THE YELLOW MEALWORM, Tenebrio molitor L.

The racemic form of 4-methyl-1-nonanol, (R)(S)-1, a sex attractant secreted by the female of the yellow mealworm, has been synthesized in 31 percent overall yield from commercially available methyl 2-octynoate, 2.Almost enantiomerically pure (R)- and (S)-1 have been stereospecifically synthesized in 21.3 and 23.9 percent overall yields, respectively, starting from methyl hydrogen (R)-3-methylglutarate, (R)-3.A precursor for (S)-1, i.e. (S)-3-methyloctanoic acid, (S)-4, has been also prepared in 84 percent yield and over 96 percent enantiomeric purity by the BF3-mediated 1,4-addition of n-pentylcopper to (-)-8-phenylmenthyl crotonate, 15, followed by saponification.The enantiomeric purities of methyl (R)-3-methyloctanoate, (R)-7, and (S)-3-methyl-1-octanol, (S)-8, have been determined by converting these compounds into (R)- and (S)-3-methyloctanoic acid, (R)-4 and (S)-4, respectively, followed by GLC analysis of the corresponding 1-(1-naphthyl)ethylamides obtained from nearly optically pure (R)-1-(1-naphthyl)ethylamine.