104086-70-6

Basic information

• Product Name: necrodol
• Synonyms: necrodol;(1S)-2,2,3,4-Tetramethyl-3-cyclopentene-1-methanol;(1R)-2,2,3α-Trimethyl-4-methylene-1β-cyclopentanemethanol;2,2,3α-Trimethyl-4-methylene-1β-cyclopentanemethanol
• CAS NO: 104086-70-6
• Molecular Formula: C10H18O
• Molecular Weight: 154.24932
• Mol File: 104086-70-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: necrodol(CAS DataBase Reference)
• NIST Chemistry Reference: necrodol(104086-70-6)
• EPA Substance Registry System: necrodol(104086-70-6)

Safety Data

• Hazardous Substances Data: 104086-70-6(Hazardous Substances Data)

Upstream product

• 120591-46-0 (1R,3R)-2,2,3-Trimethyl-4-methylene-cyclopentanecarboxylic acid methyl ester 
• 125276-86-0 (1R,3R)-2,2,3-Trimethyl-4-methylene-cyclopentanecarbaldehyde 
• 321156-42-7 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanecarboxylate 
• 321156-45-0 ethyl (1R,3S,4S)-4-hydroxy-2,2,3-trimethylcyclopentane carboxylate 
• 321156-44-9 (+)-(1R,3S)-ethyl 2,3,3-trimethyl-4-oxocyclopentanecarboxylate 
• 52486-39-2 (1R)-(-)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate 
• 127255-25-8 (1S,3S)-methyl 4-oxo-2,2,3-trimethylcyclopentanecarboxylate 
• 63721-05-1 methyl 3,3-dimethyl-4-penteneoate 
• 119548-51-5 methyl 3,3-dimethylhepta-1-ene-6-yne-4-carboxylate 
• 74866-35-6 2-(1,1-dimethylallyl)malonic acid dimethyl ester 
• 70908-42-8 α,α-dimethyl allyl methyl carbonate 
• 227596-86-3 2,2-dimethyl-5-dimethoxymethyl-3-(tert-butyldimethylsilyloxymethyl)cyclopentanone 
• 239085-69-9 3,3-dimethyl-1,4-dihydroxymethylcyclopentene 
• 239085-68-8 3,3-dimethyl-4-hydroxymethylcyclopent-1-ene-carboxaldehyde 

Downstream Products

• 104104-38-3 (3,4,5,5-tetramethylcyclopent-2-enyl)methanol 
• 135305-29-2 (-)-γ-necrodol 
• 135413-42-2 (-)-α-epi-necrodol 

Relevant articles and documents

Conversion of Campholene- to Necrodane-Type Monoterpenes. A Short Stereoselective Synthesis of (-)-(R,R)-β-Necrodol and its Three Stereoisomers

Application of a stereoselective Prins/retro-Prins rearrangement sequence from (-)-(R)-campholenyl acetate ((-)-4) opens a new access to the naturally occuring (-)-(R,R)-β-necrodol ((-)-1 and its three stereoisomers with high optical purity.

High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol

Total synthesis of the monoterpene β-necrodol has been accomplished. The key step involves an ortho-ester Claisen rearrangement in a highly sterically congested cyclopentane derivative resulting in a high level of 1,3-trans diastereoselection. A novel photo-induced decarboxylation of the obtained γ,δ-unsaturated acid afforded β-necrodol.

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.

Stereocontrolled total synthesis of (±)-β-necrodol

A total synthesis of racemic β-necrodol is described using an ortho- ester Claisen rearrangement as the key step to dictate a high level of trans- 1,3-diastereoselection on a cyclopentane derivative.

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.

A Synthesis of β-Necrodol Via A Palladium Catalyzed Reductive Enyne Cyclization

The Pd catalyzed reductive enyne cyclization provides an approach to control 1,3-diastereoselectivity and thereby provides a five step synthesis of β-necrodol, a key substituent of the defensive secretion of the red-lined carrion beetle.