81640-10-0

Basic information

• Product Name: 3-Pentanone, 1-cyclohexyl-1-hydroxy-2-methyl-, (1R,2S)-rel-
• CAS NO: 81640-10-0
• Molecular Formula: C12H22O2
• Molecular Weight: 198.305
• Mol File: 81640-10-0.mol

Chemical Properties

• CAS DataBase Reference: 3-Pentanone, 1-cyclohexyl-1-hydroxy-2-methyl-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pentanone, 1-cyclohexyl-1-hydroxy-2-methyl-, (1R,2S)-rel-(81640-10-0)
• EPA Substance Registry System: 3-Pentanone, 1-cyclohexyl-1-hydroxy-2-methyl-, (1R,2S)-rel-(81640-10-0)

Safety Data

• Hazardous Substances Data: 81640-10-0(Hazardous Substances Data)

Upstream product

• 96-22-0 pentan-3-one 
• 2043-61-0 cyclohexanecarbaldehyde 
• 17042-23-8 2-iodopentan-3-one 
• 570385-67-0 (E)-trichloro-[(1-ethylpropenyl)oxy]-silane 
• 17510-47-3 3-trimethylsilyloxy-2-pentene 
• 815-52-1 2-bromopentan-3-one 
• 100420-03-9 (4S,5R)-2,2-diethyl-4-methyl-5-phenyl-1,3-oxazolidine 
• 163073-91-4 9-((Z)-1-Ethyl-propenyloxy)-9-bora-bicyclo[3.3.1]nonane 
• 1063719-01-6 3-pentanone lithium enolate 
• 82490-58-2 rac-pent-3-yn-2-yl methanesulfonate 
• 57984-70-0 Pent-3-yn-2-ol 
• 170120-51-1 4-(TBSO)-pent-2-yne 

Downstream Products

• 1153604-76-2 (1S,2R,3S)-1-cyclohexyl-3-hydroxy-2-methylpentyl cyclohexanecarboxylate 
• 1153604-66-0 (1S,2S,3S)-1-cyclohexyl-3-hydroxy-2-methylpentyl cyclohexanecarboxylate 
• 1153604-44-4 (1R,2R,3R)-1-cyclohexyl-3-hydroxy-2-methylpentyl cyclohexanecarboxylate 
• 1153604-55-7 (1R,2S,3R)-1-cyclohexyl-3-hydroxy-2-methylpentyl cyclohexanecarboxylate 

Relevant articles and documents

Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates

Methods for the preparation of geometrically defined enoxy(trichlorosilanes) derived from ethyl ketone enolates have been developed. The addition of enoxy(trichlorosilanes) (trichlorosilyl enolates) to aldehydes proceeds with good yields in the presence of catalytic amounts of chiral phosphoramides. The reaction of Z-trichlorosilyl enolates to aryl aldehydes affords aldol products with good to excellent diastereo- and enantioselectivities. Phosphoramide-catalyzed aldol additions lacked substrate generality providing modest selectivities with unsaturated and aliphatic aldehydes. In all cases, the phosphoramide-catalyzed aldol addition of E-trichlorosilyl enolates to aldehydes provided good yields with moderate to good stereoselectivities.

Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane

Boron enolates were in situ-generated reductively by treating various α-iodo ketones such as 2-iodo-1-phenylpropan-1-one, 2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived from α-iodo ketones and pinacolatoborane were successfully isolated by distillation, though the yields were rather moderate.

Stereoselective crossed aldol reaction via boron enolate generated from α-iodoketones and 9-BBN-H

Boron enolates were in situ generated smoothly by treating α-iodo ketones with 9-BBN-H, and aldols were produced in highly diastereoselective manner by successive reaction with various aldehydes at low temperature.

Diastereoselective aldol and reformatsky reactions of α-halo carbonyl compounds and aldehydes mediated by Titanium(II) Chloride

Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.

Synthesis of β-hydroxy ketones and vinylsilanes from homopropargylic alcohols by intramolecular hydrosilation

matrix presented Catalytic intramolecular hydrosilation of nonracemic homopropargylic alcohols affords the corresponding five-membered cyclic siloxanes regiospecifically. Oxidation or alkylmetal addition converts these intermediates into β-hydroxy ketones

Catalytic, Diastereoselective Aldol Reactions Using Titanium(IV) Halides

The aldol reaction in the presence of titanium halides is described.Good yields of aldols 10-17 were obtained even with only catalytic amounts of titanium tetrafluoride.The reactions were carried out in the absence of a base. - Keywords: Aldol reaction /

Stereoselective Aldol Reaction Using Titanium Ate Complexes - An Efficient Method For Achieving Anti Aldol Selectivity

Carbonyl compounds react in the presence of titanium ate complexes in the sense of an aldol reaction.The influence of ligands on controlling stereoselection of syn and anti aldol products of the titanium ate complexes used are described.High yield of anti

HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ANTI(THREO)-ALDOLS BY THE ASYMMETRIC ALDOL REACTION UTILIZING A CHIRAL AZAENOLATE

Diastereo- and enantioselective aldol reaction between 3-pentanone and aldehydes is achieved utilizing a chiral oxazolidine derived from 3-pentanone and chiral norephedrine.The reaction of a tin(II) azaenolate generated from the chiral oxazolidine with aldehydes affords predominantly anti(threo)-aldols of high enantiomeric purity.

ERYTHRO SELECTIVE ALDOL CONDENSATION USING TITANIUM ENOLATES

Titanium enolates derived from ketones and esters react with aldehydes to afford erythro adducts with high diastereoselection.