104104-38-3

Basic information

• Product Name: trans-α-Necrodol
• Synonyms: (1R)-3,4β,5,5-Tetramethyl-2-cyclopentene-1α-methanol;trans-α-Necrodol
• CAS NO: 104104-38-3
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• Mol File: 104104-38-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: trans-α-Necrodol(CAS DataBase Reference)
• NIST Chemistry Reference: trans-α-Necrodol(104104-38-3)
• EPA Substance Registry System: trans-α-Necrodol(104104-38-3)

Safety Data

• Hazardous Substances Data: 104104-38-3(Hazardous Substances Data)

Upstream product

• 321156-42-7 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate 
• 321156-44-9 (+)-(1R,3S)-ethyl 2,3,3-trimethyl-4-oxocyclopentanecarboxylate 
• 321156-45-0 ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate 
• 104086-70-6 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanemethanol 
• 17790-69-1 2-methyl-5-oxocyclopent-1-ene-1,3-dicarboxylic acid 3-ethyl ester 1-methyl ester 
• 17790-74-8 2-methyl-4-oxo-cyclopent-2-enecarboxylic acid ethyl ester 
• 127308-44-5 (1R,2S,4R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3,3-trimethyl-1-phenylselanyl-cyclopentanecarboxylic acid methyl ester 
• 127255-42-9 (3R,5R)-1-(acetoxymethyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,4,5-trimethylcyclopentene 
• 127308-46-7 (3R,5R)-methyl 3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,4,5-trimethylcyclopentenecarboxylate 
• 127308-43-4 (1S,3R,5R)-methyl 3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,4,5-trimethylcyclopentanecarboxylate 
• 127308-47-8 (3R,5R)-1-(hydroxymethyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,4,5-trimethylcyclopentene 
• 127308-42-3 (1S,3R,5R)-methyl 3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylate 
• 127308-41-2 (1S,3R,5R)-3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylic acid 
• 104086-70-6 (-)-β-(epi)-necrodol 

Downstream Products

• 127255-48-5 α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate 
• 127308-50-3 α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate 

Relevant articles and documents

Synthesis and bioassay of racemic and chiral trans -α-Necrodyl Isobutyrate, the sex pheromone of the grape mealybug pseudococcus maritimus

A concise synthesis of the racemic form of the female-produced pheromone of the grape mealybug was developed. The synthesis was readily adapted to production of both enantiomers of the pheromone via lipase-catalyzed kinetic resolution of an intermediate in the synthesis. Replicated field trials revealed that, contrary to a preliminary report, the (R,R)- rather than the (S,S)-enantiomer is the attractive stereoisomer. Lithium aluminum hydride reduction of the insect-produced compound to α-necrodol followed by analysis on a chiral stationary phase GC column showed that the insect-produced material was actually an 85:15 mixture of the (R,R)- and (S,S)-enantiomers. The racemic form of the pheromone was highly attractive to male mealybugs, and in one of two field bioassays, the racemic material was significantly more attractive than the pure (R,R)-enantiomer, suggesting that the (S,S)-enantiomer might act synergistically.

Stereoselective conversion of campholene- to necrodane-type monoterpenes. Novel access to (-)-(R,R)- and (R,S)-α-Necrodol and the Enantiomeric γ-Necrodols

Naturally occurring (-)-(R,R)-α -necrodol ((-)-1) and its C(4)-epimer (-)-2 are obtained in 84 and 44% yields, respectively, by lithium ethylenediamide (LEDA) treatment of the corresponding β-necrodols (-)-3 and (-)-4 (Scheme I , Table), both readily available from (-)-campholenyl acetate ((-)-i) by an efficient stereoselective synthesis. The thermodynamically preferred (-)-(R)-y -necrodol ((-)-5) becomes the major product ( ≥ 80 % yield) after either prolonged treatment with LEDA or exposure of α- and β-necrodols to BF3Et2O. In an alternative route, (+)-5 is prepared starting from (+)-campholenal ((+)-ii) via Pd-catalysed decarbonylation to (-)-(S)-1,4,5,5-tetramethylcyclopent-1-ene ((-)-6) and subsequent application of an acid-catalysed CH2O-addition/ rearrangement sequence (Scheme 2).

Defense Mechanisms of Arthropods. 84. Synthesis of (-)-α-Necrodol and (-)-β-Necrodol: Novel Cyclopentanoid Terpenes from a Carrion Beetle

Syntheses of (-)-α-necrodol (1) and (-)-β-necrodol (2) from (+)-phenylcamphoric acid (7a) are described.In addition, several related compounds, (+)-epi-α-necxrodol (3), (+)-epi-β-necrodol (4), and (+)-γ-necrodol (5), have been prepared.The absolute configuration of natural α-necrodol has been established as 3R,5R by comparison of its (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl ester with the ester derived from synthetic 1.