14087-71-9

Basic information

• Product Name: (1S)-CHRYSANTHEMOLACTONE
• Synonyms: (1S)-CHRYSANTHEMOLACTONE;(1S,3R)-4,4,7,7-TRIMETHYL-3-OXABICYCLO[4.1.0]HEPTAN-2-ONE;CHRYSANTHEMOLACTONE, (1S)-;(1S)-CHRYSANTHEMOLACTONE 99+%
• CAS NO: 14087-71-9
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23
• Mol File: 14087-71-9.mol

Chemical Properties

• Melting Point: 80-83 °C
• Boiling Point: 257.18°C (rough estimate)
• Flash Point: 90.1°C
• Appearance: /
• Density: 0.9812 (rough estimate)
• Vapor Pressure: 0.0496mmHg at 25°C
• Refractive Index: 1.5070 (estimate)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: (1S)-CHRYSANTHEMOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-CHRYSANTHEMOLACTONE(14087-71-9)
• EPA Substance Registry System: (1S)-CHRYSANTHEMOLACTONE(14087-71-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 14087-71-9(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW-BEIGE CRYSTALS

InChI:InChI=1/C10H16O2/c1-9(2)5-6-7(8(11)12-9)10(6,3)4/h6-7H,5H2,1-4H3/t6-,7-/m1/s1

Upstream product

• 26771-06-2 (-)-cis-chrysanthemic acid 
• 62445-40-3 (1S,3R)-3-(2-Hydroxy-2-methyl-propyl)-2,2-dimethyl-cyclopropanecarboxylic acid 
• 85710-57-2 (3R)-3-(1-Chloro-1-methylethyl)-5-methylhexan-5-olide 
• 141342-66-7 (1S,3R)-2,2-dimethyl-3-(2-hydroxy-2-methylpropyl)cyclopropanecarbonitrile 
• 498-15-7 (+)-Δ³-carene 
• 6617-36-3 (+)-1S,6R-car-2-en-4-one oxime 
• 77715-91-4 3c-acetonyl-2,2-dimethyl-cyclopropane-r-carboxylic acid 
• 6617-33-0 (1E,6R)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-one 
• 77704-82-6 (1R,3S,6S)-3,4,7,7-Tetramethyl-bicyclo[4.1.0]hept-4-en-3-ol 
• 110847-02-4 [(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-cyclopropyl]-acetonitrile 
• 141342-64-5 (1R,3S)-2,2-dimethyl-3-cyanocyclopropaneacetonitrile 
• 14087-76-4 (1S,3R)-3-(2-Hydroxy-2-methyl-propyl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester 
• 124-38-9 carbon dioxide 
• 38614-36-7 2-methylpropen-1-ylmagnesium bromide 

Downstream Products

• 473-50-7 pyrocin 
• 2935-23-1 cis-Chrysanthemic acid 

Relevant articles and documents

Studies of Chrysanthemic Acid Derivatives: Catalyses Reactions of 3-(2-Hydroxymethyl-3,3-dimethylcyclopropyl)-2-methylpropanol and Formation of a Novel Eight-membered Cyclic Sulphite

Acid catalysed reaction of the cyclopropanediol (3) derived from cis-chrysanthemic acid cis-(1) afforded, depending on the reaction conditions, 3-vinyl-2,2,5,5-tetramethyltetrahydrofuran (4) and 4,4,7,7-tetramethyl-3-oxabicycloheptane (5).On treatment with thionyl chloride-pyridine complex there was obtained in addition the eight-membered cyclic sulphite, 6,6,9,9-tetramethyl-3,5-dioxa-4-thiabicyclononane 4-oxide (6).X-Ray analysis confirms a boat-chair conformation with the S=O group trans to the cyclopropane ring in an equatorial situation.Thermal reaction of (6) gave either (4) or a mixture of (5), cis-chrysanthemol (7), and cis-isochrysanthemol (8).

Electrooxidative Cleavage of Carbon-Carbon Bonds. 2. Double Cleavage of α,β-Epoxyalkanones and Enantiospecific Syntheses of Chiral Methyl trans- and cis-Chrysanthemates from (+)- and (-)-Carvones

The stereospecific synthesis of chiral methyl trans- and cis-chrysanthemates (1 and 26) from (+)- and (-)-carvones (7a,b) is described.Methyl (3R)- and (3S)-3-(1-chloro-1-methylethyl)-5-oxohexanoates (3) and methyl (3S)- and (3R)-3-(1-chloro-1-methylethyl

ROUTES TO trans-CHRYSANTHEMIC ACID. IV. SYNTHESIS FROM 4-ACETYL-2-CARENE

4-Acetyl-2-carene obtained from 3-carene undergoes methylation, ozonolysis, and lead tetraacetate oxidation resulting in cis-dihydrochrysanthemolactone.

STEREOSPECIFIC CYCLOPROPENIC SYNTHESIS OF CIS-CHRYSANTHEMIC METHYL ESTER. 2. THE BY-PASSING DIAZOALKANE WAY (1).

A stereospecific synthesis of cis-chrysanthemate by catalytic hydrogenation of a cyclopropene is described.The required precursor, a 3H-pyrazole, is obtained here via a novel dianion reaction and MnO2 dehydrogenation of a Δ2-pyrazoline, instead of the more cumbersome diazoaddition method.

Addition of Organomagnesium Halides to C = C Bonds, XVI. - A Synthetic Route to Chrysanthemic Acid

Addition of 1-isobutenylmagnesium bromide (4) to 3,3-dimethylcyclopropene leads to the formation of a 1:1 product as well as considerable amounts of 1:2, 1:3, and higher molecular adducts.Further reaction with carbon dioxide gives, after hydrolysis, a mixture of cis-chrysanthemic acid (6; 39percent) and the higher molecular acids 1 and 2.