76793-01-6

Basic information

• Product Name: (1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol
• CAS NO: 76793-01-6
• Molecular Formula: C₁₄H₂₅NO₂
• Molecular Weight: 239.3538
• Mol File: 76793-01-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 335.7°C at 760 mmHg
• Flash Point: 156.9°C
• Density: 1.1g/cm³
• Vapor Pressure: 8.15E-06mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: (1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol(76793-01-6)
• EPA Substance Registry System: (1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol(76793-01-6)

Safety Data

• Hazardous Substances Data: 76793-01-6(Hazardous Substances Data)

Usage

General Description

(1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol is a chemical compound with a complex molecular structure. It is a bicyclic organic compound that contains a five-membered ring with an additional oxygen atom, as well as a pyrrolidine ring and a hydroxyl group. The compound is a chiral molecule with four stereocenters, giving rise to multiple possible stereoisomers. (1R,4R,5S,6S)-1,3,3-trimethyl-6-(pyrrolidin-1-yl)-2-oxabicyclo[2.2.2]octan-5-ol is likely to have biological activity and potential medicinal use due to its complex structure and the presence of a pyrrolidine moiety, which is a common structural element in many pharmaceuticals and natural products. The compound's structure suggests potential involvement in neurological or physiological processes due to the presence of the pyrrolidine ring and the hydroxyl group.

Upstream product

• 76735-19-8 (1R,4S,5R,6S)-1,3,3-Trimethyl-6-pyrrolidin-1-yl-2-oxa-bicyclo[2.2.2]octan-5-ol 
• 76735-24-5 1,3,3-trimethyl-6-cis-pyrrolidin-1-yl-2-oxabicyclo<2.2.2>octan-5-one 
• 31316-33-3 1-((1R,4S)-1,3,3-Trimethyl-2-oxa-bicyclo[2.2.2]oct-5-en-6-yl)-pyrrolidine 

Downstream Products

• 76735-19-8 (1R,4S,5S,6S)-1,3,3-Trimethyl-6-pyrrolidin-1-yl-2-oxa-bicyclo[2.2.2]octan-5-ol 

Relevant articles and documents

Carbonyl Transposition and Regio- and Stereo-specific Syntheses of New Alcohols, Amino-alcohols, and Ketones in the Monoterpenoid 1,3,3-Trimethyl-2-oxabicyclooctane

An efficient transposition of carbonyl group R1-CO-CH2-R2 -> R1-CH2-CO-R2 in the 1,3,3-trimethyl-2-oxabicyclooctane system was carried out via hydroboration-oxidation of 6-dialkylamino-1,3,3-trimethyl-2-oxabicyclooct-5-enes (3a-c), which gave regio- and stereo-specifically 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ols (4a-c) in high yield.Cope reaction on the N-oxide (5b) obtained from the amino-alcohol (4b) with hydrogen peroxide led to 1,3,3-trimethyl-2-oxabicyclooctan-5-one (6), the other possible isomer of the long-known 1,3,3-trimethyl-2-oxabicyclooctan-6-one (1b).The ketone (6) was also obtained from 1,3,3-trimethyl-2-oxabicyclooct-5-ene (2) via its trans-epoxide (11), lithium aluminium hydride reduction at 160-165 deg C of which gave stereo- and regio-specifically 1,3,3-trimethyl-2-oxabicyclooctan-5-trans-ol (9b).Chromic acid oxidation of (9b) and (4a-c) under various conditions gave the ketone (6) and the amino-ketones (7a-c), respectively.Lithium aluminium hydride reduction of (6) and (7a-c) afforded stereospecifically the cis-alcohol (9a) and 6-cis-dialkylamino-1,3,3-trimethyl-2-oxabicyclooctan-5-cis-ols (8a-c), respetively.Hydroboration-oxidation of the alkene (2) was not regiospecific, giving a 3:1 mixture of the trans-alcohols (9b) and (10b), respectively.