55339-40-7

Basic information

• Product Name: (3-oxo-cyclohexyl)-acetaldehyde
• Synonyms: (3-oxo-cyclohexyl)-acetaldehyde
• CAS NO: 55339-40-7
• Molecular Weight: 140.182
• Mol File: 55339-40-7.mol

Chemical Properties

• CAS DataBase Reference: (3-oxo-cyclohexyl)-acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (3-oxo-cyclohexyl)-acetaldehyde(55339-40-7)
• EPA Substance Registry System: (3-oxo-cyclohexyl)-acetaldehyde(55339-40-7)

Safety Data

• Hazardous Substances Data: 55339-40-7(Hazardous Substances Data)

Upstream product

• 930-68-7 cyclohexenone 
• 20498-05-9 3-allylcyclohexanone 
• 7422-90-4 acetaldehydedimethylhydrazone 

Downstream Products

• 208349-24-0 3-(1'-hydroformyl-1'-ethenyl)cyclohexanone 
• 108329-93-7 methyl 2-((S)-3-oxocyclohexyl)acetate 
• 177770-85-3 (R)-3-methoxycarbonylmethylcyclohexanone 

Relevant articles and documents

Bicyclo[3.2.1]Octanes via McMurry couplings

A novel approach to the synthesis of bicyclo[3.2.1]octane systems is described. The key step involves the McMurry coupling of ketoaldehyde 7 which leads to the bridgehead dihydroxybicyclo[3.2.1]octane 8.

Efficient and convenient method for workup of ozonolysis reaction using sodium hydrosulfite

An efficient and convenient method is reported for reductive workup of the ozon-olysis reaction using sodium hydrosulfite. Comparisons were made between triethylamine and methyl sulfide for their use as a quenching reagent in the ozonolysis of a variety of alkenes. Taylor & Francis Group, LLC.

The mechanistic study and synthetic applications of the base treatment in the ozonolytic reactions

The E1cb mechanism is the overwhelming process in the reaction of bases and ozonides. As a quenching agent in the ozonolysis of a variety of alkenes, the reactions involving triethylamine often gave better yields and proceeded faster than those involving methyl sulfide. On the other hand, in the presence of 4 A molecular sieves, the secondary amines reacted with mono- and 1,1-di-substituted ozonides to afford the reductive amination products in high yields. The formation of ammonium formate in the reaction mixture also supported the E1cb mechanism in the reaction of ozonide and amine.

Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones

The asymmetric Michael addition reaction of chiraly modified P-allyl anions derived from enantiomerically ebriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones.The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones.With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90percent diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series).The Michael reaction of the anions derived from the trans series were not diastereoselective (ca. 10percent diastereomeric excess).The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.

A convenient and efficient workup of ozonolysis reactions using triethylamine

Comparisons were made between triethylamine and methyl sulfide for their use as a quenching agent in the ozonolysis of a variety of alkenes. The reactions involving triethylamine often gave better yields and proceeded faster than those of involving methyl sulfide. The role of triethylamine played as base instead of reducing agent in the reaction.