10309-65-6

Basic information

• Product Name: [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate
• Synonyms: [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate
• CAS NO: 10309-65-6
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.2854
• EINECS: 233-684-6
• Mol File: 10309-65-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 263.3°Cat760mmHg
• Flash Point: 98.8°C
• Appearance: /
• Density: 1.1g/cm³
• CAS DataBase Reference: [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate(10309-65-6)
• EPA Substance Registry System: [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate(10309-65-6)

Safety Data

• Hazardous Substances Data: 10309-65-6(Hazardous Substances Data)

Usage

General Description

The chemical "[1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate" is a bicyclic compound with a hydroxyl group and an acetate group attached to it. Its molecular structure contains a bicyclo[4.1.0]heptane ring system with three methyl groups and a hydroxyl group located at specific positions within the ring. The acetate group is attached to the hydroxyl group, forming an ester. [1S-(1alpha,3beta,4alpha,6alpha)]-3-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-4-yl acetate may have applications in organic synthesis and pharmaceutical research, and its specific structure and properties make it potentially useful in the development of new chemical compounds and materials.

Upstream product

• 64-19-7 acetic acid 
• 936-91-4 3-carene epoxide 
• 57400-93-8 3β-acetoxycaran-4α-ol 
• 22556-08-7 trans-3,4-caranediol 
• 108-24-7 acetic anhydride 

Downstream Products

• 6380-28-5 carvacryl acetate 
• 4017-83-8 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol 
• 10481-91-1 (+)-4-trans-isopropylene-1-methylbicyclo<3.1.0>hexan-cis-2-ol 

Relevant articles and documents

THE ALDOL-TYPE CONDENSATION OF LITHIUM, BORON AND TITANIUM ENOLATES OF ISOCARANYL ACETATES WITH BENZALDEHYDE. THE METAL AND CHIRAL AUXILIARY EFFECTS

A new approach to chiral enolates by using a chiral ester (isocaranyl acetates) and a chiral organometallic reagent (boranes and titanates) is reported.The effect of this double enantiodifferentiation and the effects of the isomerism of chiral auxiliary (2- and 4-isocaranyl) and that of the metal (Li, B, Ti) on the enantioselectivity of aldol condensation of 2- and 4-isocaranyl acetates with benzaldehyde are discussed.Lithium and boron enolates of isocaranyl acetates add preferentially to the si-face of benzaldehyde while the addition of analogous titanium enolates occurs preferably on the re-face of the aldehyde.The enolborinate which gives the highest ee value is that obtained by transmetallation reaction of the lithium enolate of (+)-2-isocaranyl acetate with (-)-di-4-isocaranylchloroborane.Obversely the enoltitanate prepared from (-)-4-isocaranyl acetate and the LDA-(+)-di-2-isocaranoxy(chloro)cyclopentadienyl titanate system is that which gives the highest enantiofacial discrimination.The chiral auxiliary effect has been used to plan the synthesis of (+)-4α-acetoxy-3β-trimethylsilyloxy-trans-carane, the titanium enolate of which gives (R)-(+)-β-hydroxy-β-phenylpropionic acid in high enantiomeric excess.