76735-21-2

Basic information

• Product Name: (1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol
• CAS NO: 76735-21-2
• Molecular Formula: C₁₄H₂₅NO₃
• Molecular Weight: 255.3532
• Mol File: 76735-21-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 361.4°C at 760 mmHg
• Flash Point: 172.4°C
• Density: 1.128g/cm³
• Vapor Pressure: 1.11E-06mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: (1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol(76735-21-2)
• EPA Substance Registry System: (1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol(76735-21-2)

Safety Data

• Hazardous Substances Data: 76735-21-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol" is a complex organic molecule with a bicyclic structure. It contains three methyl groups, a morpholine ring, and an alcohol functional group. The compound has a stereochemistry denoted by the (1R,4R,5R,6S) designation, indicating the specific arrangement of atoms around the carbon atoms in the molecule. The morpholine group contributes to the compound's heterocyclic structure, and the presence of an alcohol group indicates potential reactivity in chemical reactions. (1R,4R,5R,6S)-1,3,3-trimethyl-6-(morpholin-4-yl)-2-oxabicyclo[2.2.2]octan-5-ol may have pharmaceutical or industrial uses, and its unique structure may make it valuable for medicinal or synthetic applications.

Upstream product

• 76735-21-2 (1R,4S,5R,6S)-1,3,3-Trimethyl-6-morpholin-4-yl-2-oxa-bicyclo[2.2.2]octan-5-ol 
• 31316-32-2 4-((1R,4S)-1,3,3-Trimethyl-2-oxa-bicyclo[2.2.2]oct-5-en-6-yl)-morpholine 
• 76735-26-7 1,3,3-trimethyl-6-cis-morpholino-2-oxabicyclo<2.2.2>octan-5-one 

Downstream Products

• 76735-21-2 (1R,4S,5S,6S)-1,3,3-Trimethyl-6-morpholin-4-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.