41654-15-3

Basic information

• Product Name: METHYLCIS-5-OCTENOATE
• Synonyms: METHYLCIS-5-OCTENOATE;(Z)-5-Octenoic acid methyl ester;Methyl (5Z)-octenoate;methyl (Z)-5-octenoate
• CAS NO: 41654-15-3
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• Mol File: 41654-15-3.mol

Chemical Properties

• Boiling Point: 195℃(760 Torr)
• Flash Point: 73℃ (760 Torr)
• Appearance: /
• Density: 0.896±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.425mmHg at 25°C
• Refractive Index: 1.436
• CAS DataBase Reference: METHYLCIS-5-OCTENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLCIS-5-OCTENOATE(41654-15-3)
• EPA Substance Registry System: METHYLCIS-5-OCTENOATE(41654-15-3)

Safety Data

• Hazardous Substances Data: 41654-15-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid; dairy, coconut aroma.

InChI:InChI=1/C9H16O2/c1-3-4-5-6-7-8-9(10)11-2/h4-5H,3,6-8H2,1-2H3/b5-4-

Upstream product

• 40564-10-1 2-propylidene-cyclopentanone 
• 67-56-1 methanol 
• 41653-97-8 (Z)-oct-5-enoic acid 
• 684-93-5 1-methyl-1-nitrosourea 
• 64275-73-6 (Z)-oct-5-en-1-ol 
• 76469-08-4 5-octynolic acid 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 123-38-6 propionaldehyde 
• 186581-53-3 diazomethane 

Downstream Products

• 64275-73-6 (Z)-oct-5-en-1-ol 
• 34010-15-6 cis-11-tetradecen-1-ol 
• 20711-10-8 (Z)-11-tetradecenyl acetate 

Relevant articles and documents

Investigating the nature of palladium chain-walking in the enantioselective redox-relay heck reaction of alkenyl alcohols

The mechanism of the redox-relay Heck reaction was investigated using deuterium-labeled substrates. Results support a pathway through a low energy palladium-alkyl intermediate that immediately precedes product formation, ruling out a tautomerization mechanism. DFT calculations of the relevant transition structures at the M06/LAN2DZ+f/6-31+G level of theory show that the former pathway is favored by 5.8 kcal/mol. Palladium chain-walking toward the alcohol, following successive β-hydride eliminations and migratory insertions, is also supported in this study. The stereochemistry of deuterium labels is determined, lending support that the catalyst remains bound to the substrate during the relay process and that both cis- and trans-alkenes form from β-hydride elimination. (Chemical equation presented).

Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

Palladium- and ruthenium-catalyzed cycloisomerization of enynamides and enynhydrazides: A rapid approach to diverse azacyclic frameworks

I want to ride my azacycle: The title reaction of enynamides affords a wide diversity of azacycles. The reactions are high-yielding, highly stereoselective, and proceed rapidly under mild reaction conditions. Equivalent transformations using enynhydrazides offer new routes to pyrazole and indazole scaffolds. Boc=tert-butoxycarbonyl, EWG=electron-withdrawing group, Ns=4-nitrobenzenesulfonyl, Ts=4-toluenesulfonyl. Copyright

Enzymes in organic synthesis. 27: Lipase-catalyzed synthesis of (5R,6S)-6-acetoxyalkan-5-olides - Homologues of the mosquito oviposition attractant pheromone

Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysi