95335-91-4

Basic information

• Product Name: D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL
• Synonyms: d-α,β-cyclohexylideneglycerol;D-alpha,beta-Cyclohexylideneglycerol;2,2-PentaMethylidene-4-hydroxyMethyl-1,3-dioxolane;1,4-Dioxaspiro[4.5]decane-2-Methanol, (S)-;[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]methanol
• CAS NO: 95335-91-4
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22
• Mol File: 95335-91-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 118-120 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00396mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: 2-8°C
• BRN: 108000
• CAS DataBase Reference: D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL(CAS DataBase Reference)
• NIST Chemistry Reference: D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL(95335-91-4)
• EPA Substance Registry System: D-ALPHA BETA-CYCLOHEXYLIDENE-GLYCEROL(95335-91-4)

Safety Data

• WGK Germany: 3
• F: 9-23
• Hazardous Substances Data: 95335-91-4(Hazardous Substances Data)

Usage

Uses

D-α,β-Cyclohexylideneglycerol can be used:As an intermediate in the synthesis of antiarrhythmic oral drugs: (+)- and (?)-mexiletine.As a precursor in the preparation of glycoglycerolipids.As an intermediate in the synthesis of (S)-hydroxymethyl-1,4-benzodioxane, a key intermediate for the preparation of α-adrenergic receptor antagonists, and antidepressant drug doxazosin.

InChI:InChI=1/C9H16O3/c10-6-8-7-11-9(12-8)4-2-1-3-5-9/h8,10H,1-7H2/t8-/m0/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 108-94-1 cyclohexanone 
• 56-81-5 glycerol 

Downstream Products

• 130028-47-6 2-(2,4-Dinitro-phenoxymethyl)-1,4-dioxa-spiro[4.5]decane 
• 130028-44-3 4-(1,4-Dioxa-spiro[4.5]dec-2-ylmethoxy)-benzonitrile 
• 4167-35-5 (1,4-Dioxa-spiro[4.5]dec-2-yl)-methanol 
• 113798-80-4 (R)-(1,4-dioxaspiro[4.5]dec-2-yl)methanol 
• 78008-36-3 (R)-2,3-cyclohexylideneglyceraldehyde 
• 1638138-12-1 ((R)-2,2-cyclohexylidine-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulphonate 
• 124933-36-4 toluene-4-sulfonic acid 1,4-dioxaspiro[4,5] dec-2-yl-methyl ester 
• 82372-20-1 (1,4-dioxaspiro[4.5]decan-2-yl)methyl benzoate 
• 1386397-41-6 C₁₅H₂₀O₂Se 
• 1236037-87-8 3-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-1,2-O-cyclohexylidene-sn-glycerol 
• 1227612-77-2 3-O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-cyclohexylidene-sn-glycerol 

Relevant articles and documents

Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions

Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright

Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline

A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline.

EFFICIENT RESOLUTION OF SECONDARY ALCOHOLS, CYANOHYDRINS, AND GLYCEROL ACETALS BY COMPLEXATION WITH THE HOST DERIVED FROM TARTARIC ACID

Some title hydroxy compounds were resolved efficiently by complexation with the host compounds derived from tartaric acid.