5700-74-3

Usage

Uses

Used in Cleaning Products and Detergents:
ETOC-PRO-OH is used as a surfactant and emulsifier for enhancing the cleaning and foaming properties of cleaning products and detergents. Its ability to reduce surface tension allows for better spread and penetration, improving the overall effectiveness of these products.
Used in Personal Care Products:
In the personal care industry, ETOC-PRO-OH is used as an ingredient in cosmetics and other formulations to improve their texture, stability, and performance. Its emulsifying properties help in creating stable mixtures of oil and water, which is essential for many personal care products.
Used in Solubilizing Hydrophobic Substances:
ETOC-PRO-OH is used as a solubilizing agent in water-based formulations to incorporate oils and other hydrophobic substances. This is particularly useful in the pharmaceutical and chemical industries where water-soluble formulations are required.
Used in Environmentally Friendly Formulations:
Due to its less toxic nature and biodegradability, ETOC-PRO-OH is used as a preferred surfactant and emulsifier in environmentally conscious formulations, reducing the environmental impact of various products.

InChI:InChI=1/C8H13NO4/c1-2-13-8(12)9-5-3-4-6(9)7(10)11/h6H,2-5H2,1H3,(H,10,11)

Upstream product

• 147-85-3 L-proline 
• 74877-64-8 ethyl α-methoxyvinyl carbonate 
• 541-41-3 chloroformic acid ethyl ester 
• 147-85-3 L-proline 

Downstream Products

• 1238965-61-1 (S)-1-ethoxycarbonyl-2-(4-fluorobenzoyl)pyrrolidine 
• 1008530-28-6 (S)-ethyl 2-((S)-1-((R)-4-benzyl-4,5-dihydrooxazol-2-yl)-2-methylpropylcarbamoyl)pyrrolidine-1-carboxylate 
• 1187560-75-3 2-[bis(4-trifluoromethylphenyl)hydroxymethyl]pyrrolidine-1-carboxylic acid ethyl ester 
• 1187560-71-9 2-[bis(3,5-bis(trifluoromethyl)phenyl)hydroxymethyl]pyrrolidine-1-carboxylic acid ethyl ester 
• 360068-90-2 (S)-(-)-α,α-di(4-vinylphenyl)-2-[(N-ethoxycarbonyl)pyrrolidine]methanol 
• 110529-25-4 (S)-α-<(S)-pyrrolidin-2-yl>benzyl alcohol hydrochloride 
• 145057-61-0 N-ethoxycarbonyl-L-prolyl-(1-hydroxy)-cyclohexyl diazoethane 
• 145057-79-0 2-N-ethoxycarbonyl-L-prolyl-cyclohexanone 
• 152326-82-4 ethyl (S)-(-)-2--1-pyrrolidinecarboxylate 
• 22348-32-9 (S)-diphenylprolinol 
• 110529-26-5 (1S,2'S)-phenyl(1-neopentylpyrrolidin-2-yl)methanol 
• 110529-24-3 (1R,2'S)-phenyl(1-neopentylpyrrolidin-2-yl)methanol 
• 110529-23-2 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 
• 74936-98-4 (1S,2'S)-phenyl(1-methylpyrrolidin-2-yl)methanol 

Relevant academic research and scientific papers

Organocatalytic Enantioselective Continuous-Flow Cyclopropanation

A set of six solid-supported diarylprolinol catalysts (varying on the anchoring strategy and the type of polymeric support) has been prepared and applied to the enantioselective cyclopropanation reaction. The selected candidate allows implementation of a long flow experiment (48 h) and generates a library of 12 cyclopropanes by sequential flow experiments. The mildness and utility of the method have enabled a telescoped process in which the outstream is directly used in a Wittig flow reaction.

Diastereoselective synthesis of (R)-phenanthrenyl-9yl-[(S)-pyrrolidin-2yl)] methanol

A four-step synthesis of sterically demanding (R)-phenanthren-9-yl-[(S)- pyrrolidin-2-yl] methanol has been easily accomplished starting from L-proline in high diastereoselectivity. These compounds are potentially useful ligands in metal-catalyzed reactio

Stereocontrolled solid-phase synthesis of oligonucleoside H-phosphonates by an oxazaphospholidine approach

(Chemical Equation Presented) Stereodefined oligonucleoside H-phosphonates were synthesized on a solid support using diastereopure nucleoside 3′-O-oxazaphospholidine monomers. Several stereodefined backbone-modified analogues were obtained with the oligonucleoside H-phosphonates as precursors (see scheme; BPRO = protected nucleobase, DMTr = 4,4′- dimethoxytrityl, Th = thymin-1-yl, TfO- = triflate).

Synthesis and resolution of 2,2-dimethyl-1,3-diphenyl-1,3-propanediol, a new C2-symmetric and conformationally rigid acyclic diol

Diastereomerically pure (+)- and (-)-2,2-dimethyl-1,3-diphenyl-1,3-propanediols were synthesized starting from diethyl malonate and resolved through diesters of (-)-camphanic acid and also N-carbethoxy-L-proline. The absolute configuration of the (-)-enantiomer was established by X-ray crystallography.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 17. Preparation of aliphatic amino acid derived γ-alkoxycarbonyl-amino-β-oxo ylides and pyrolysis to give α,β-acetylenic γ-amino acid and GABA analogues

A series of eleven α-aminoacyl stabilised phosphorus ylides 9-19 have been prepared by condensation of N-alkoxycarbonyl protected amino acids with Ph3P = CHCO2Et using a carbodiimide peptide coupling reagent. Upon flash vacuum pyrolysis at 600 °C, these undergo extrusion of Ph3PO to give the corresponding α,β-acetylenic γ-amino esters 21-29, 33 and 34 in moderate yield. In two cases the terminal alkynes 30 and 31 are also formed. The β-aminoacyl ylide 20 from β-alanine similarly gives the α,β-acetylenic δ-amino ester 35 upon pyrolysis. Regioselective addition of HBr to the triple bond of one acetylenic ester 25 was observed giving a mixture of E and Z α-bromoacrylates 36. Hydrogenation of the N-Cbz acetylenic esters 21-23 and 33 results in N-deprotection and hydrogenation of the triple bond to afford the chiral GABA analogues 37-40 in 70 ->95% ee as determined by 19F NMR of their Mosher amides. Fully assigned 13C NMR spectra of all the ylides and acetylenic ester derivatives are presented.

Convenient method for the synthesis of chiral α,α-diphenyl-2-pyrrolidinemethanol

A simplified, convenient synthesis of chiral α,α-diphenyl-2-pyrrolidine-methanol involving one step N-and O-protection of S-proline using ethylchloroformate followed by Grignard addition-alkaline hydrolysis (KOH/CH3OH) is described.

Synthesis of Chiral N-Protected α-Amino-β-Diketones from α-Diazoketones Derived from Natural Amino Acids

α-Diazoketols, prepared by condensation of aldehydes or ketones with lithiated optically active α-diazoketones derived from natural amino acids, rearrange to homochiral α-amino-β-diketones on treatment with rhodium(II) acetate.

Asymmetric Synthesis of Optically Active threo- and erythro-Pyrrolidinylbenzyl Alcohol by the Highly Stereospecific Arylation of (S)-Proline and the Subsequent Highly Diastereoselective Reduction of the α-Amino Ketone

Optically active α-amino phenyl ketones in 92-94percent enantiomeric excess (e.e.) were obtained from the stereospecific arylation of (S)-proline or its derivatives by Friedel-Crafts reaction of by Grignard reaction.The subsequent complementary diastereoselective reductions of the α-amino ketone afforded respectively (S)- and (R)-α-benzyl alcohol in 93-100percent e.e. and in 100percent diastereoisomeric excess.The stereochemical course of the reduction of the α-amino ketone is discussed.

Catalytic Asymmetric Induction. Highly Enantioselective Addition of Dialkylzincs to Aldehydes Using Chiral Pyrrolidinylmethanols and Their Metal Salts

A series of chiral pyrrolidinylmethanols were synthesized from (S)-proline.Optically active secondary alcohols (R and S enantiomers, respectively) in up to 100percent enantiomeric excess (ee) were obtained in high yields from the enantioselective addition of dialkylzincs to aldehydes catalyzed by 2-5 mol percent of chiral pyrrolidinylmethanols.The sense of the asymmetric induction and the degrees of enantioselectivities were highly dependent on the structure of the catalysts. (+)-DPMPM (3, tertiary amino tertiary alcohol) catalyzed the reaction of aryl, α,β-unsaturated, and aliphatic aldehydes to afford (S) alcohols in high ee's.When the lithium salt of 3 was employed as catalyst in the reactions of aryl and α,β-unsaturated aldehydes, the ee's of (S) alcohols reached 100percent.On the other hand, (-)-erythro-PNPM (10, tertiary amino secondary alcohol) afforded (R) alcohols in high ee (100percent ee).The steric course of the reaction is discussed.