15914-84-8

Basic information

• Product Name: (S)-(-)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL
• Synonyms: (S)-(-)-1-(1-NAPHTHYL)ETHANOL;(S)-1-NAPHTHALEN-1-YL-ETHANOL;(S)-(-)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL;(s)-(-)-α-methyl-1-naphthalenemethanol;s-(-)-α-methyl-1-naphthalenemethanol;S-(-)-1-(1-NAPTHALENYL)ETHANOL;(S)-1-Naphthylethanol;(1S)-1-(1-Naphthyl)ethanol
• CAS NO: 15914-84-8
• Molecular Formula: C₁₂H₁₂O
• Molecular Weight: 172.22
• EINECS: 1592732-453-0
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 15914-84-8.mol
• Article Data: 275

Chemical Properties

• Melting Point: 47-49 °C(lit.)
• Boiling Point: 165°C/11mmHg(lit.)
• Flash Point: 145.346 °C
• Appearance: Yellow/Powder
• Density: 1.114 g/cm³
• Vapor Pressure: 0.000177mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.29±0.20(Predicted)
• BRN: 2045009
• CAS DataBase Reference: (S)-(-)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL(15914-84-8)
• EPA Substance Registry System: (S)-(-)-ALPHA-METHYL-1-NAPHTHALENEMETHANOL(15914-84-8)

Safety Data

• Statements: 22-24/25
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 15914-84-8(Hazardous Substances Data)

Usage

Chemical Properties

White fine crystalline powder

Uses

(S)?-?1-?(Naphthalen-?1-?yl)?ethanol is a building block used in the synthesis of novel 2,4-diaminoquinazoline derivatives as SMN2 promoter activators for the potential treatment of spinal muscular atrophy.

Purification Methods

Purify the alcohol by recrystallisation from Et2O/pet ether, Et2O, hexane [Balfe et al. J Chem Soc 797 1946, IR, NMR: Theisen & Heathcock J Org Chem 53 2374 1988, see also Fredga et al. Acta Chem Scand 11 1609 1957]. The RS-alcohol [57605-95-5] has m 63-65o, 65-66o from hexane. [Beilstein 6 III 3034, 6 IV 4346.]

InChI:InChI=1/C12H12O/c1-9(13)11-8-4-6-10-5-2-3-7-12(10)11/h2-9,13H,1H3/t9-/m0/s1

Synthetic route

1'-naphthacetophenone (941-98-0) → (S)-1-(1-Naphthyl)ethanol (15914-84-8)

Conditions	Yield
With [(R,R,R)-Ru(BINAP-PO3H2)(DPEN)Cl2] on magnetite nanoparticle; potassium tert-butylate; hydrogen In isopropyl alcohol at 20℃; under 36200.4 Torr; for 20h;	100%
With potassium hydroxide; (R,R)-1,2-diphenylethylenediamine; hydrogen; [RuCl2((R)-3,3'-dm-binap)(dmf)n] In isopropyl alcohol at 20℃; under 6080 Torr;	99%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C53H73FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 60℃; under 22801.5 Torr; for 12h; Autoclave; enantioselective reaction;	99%

1'-naphthacetophenone (941-98-0) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With dimethylsulfide borane complex; (S)-2-(anilinodiphenylmethyl)pyrrolidine In tetrahydrofuran at 20℃; for 2h; enantioselective reaction;	A n/a B 99%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 2h; enantioselective reaction;	A n/a B 99%
With (mer-[(S,S)-1,5-dimethyl-2,4-bis(4-phenyl-1,3-oxazolin-2-yl)benzene(1-)]Ru(CO)Cl)2(ZnCl2); hydrogen; sodium methylate In isopropyl alcohol at 40℃; under 22801.5 Torr; for 24h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction;	A 96% B n/a

vinyl propionate (105-38-4) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(1-naphtnyl)ethyl propionate

Conditions	Yield
With Novozyme 435 In toluene at 34℃; for 15h; Enzymatic reaction;	A 97.8% B n/a

Isopropenyl acetate (108-22-5) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With Candida antarctica lipase B; dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); potassium tert-butylate; sodium carbonate In tetrahydrofuran; toluene at 20℃; for 24h;	A n/a B n/a C 97%
With lipase B from Candida antarctica In neat (no solvent) for 4h; Milling; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C n/a

2,2,2-trichloroethyl butyrate (57392-44-6) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(1'-naphthyl)ethyl butyrate (113794-42-6)

Conditions	Yield
With porcine pancreatic lipase In n-heptane at 60℃; for 336h;	A 94% B 96%

vinyl n-butyrate (123-20-6) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(1'-naphthyl)ethyl butyrate (113794-42-6)

Conditions	Yield
With Novozyme 435 In toluene at 37℃; for 18h; Enzymatic reaction;	A 95.4% B n/a

vinyl valerate (5873-43-8) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + C17H20O2

Conditions	Yield
With Novozyme 435 In toluene at 40℃; for 20h; Enzymatic reaction;	A 90.3% B n/a

vinyl octanoate (818-44-0) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + C20H26O2 (1369869-20-4)

Conditions	Yield
With lipase B from Candida antarctica In cyclohexane at 50℃; for 1.75h; Resolution of racemate; optical yield given as %ee;	A n/a B 90%

dimethyl zinc(II) (544-97-8) + 1-naphthaldehyde (66-77-3) → (S)-1-(1-Naphthyl)ethanol (15914-84-8)

Conditions	Yield
Stage #1: dimethyl zinc(II); 1-naphthaldehyde With N,N-bis(3,5-di-t-butylbenzyl)-O-benzyl-L-α-aspartyl-L-proline methyl ester In toluene at 0 - 20℃; for 48h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene Inert atmosphere; optical yield given as %ee; enantioselective reaction;	74%

1-(1-naphthyl)ethanol (57605-95-5) → 1'-naphthacetophenone (941-98-0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 0℃; Electrochemical reaction; optical yield given as %ee; enantioselective reaction;	A 62% B n/a C n/a
With palladium dichloro (η-2,5-norbornadiene); oxygen; (-)-sparteine In toluene at 80℃; for 192h; Title compound not separated from byproducts;	A 54% B n/a C n/a
With 3 A molecular sieve; oxygen; (-)-sparteine; palladium dichloro (η-2,5-norbornadiene) In toluene at 80℃; under 760 Torr; for 192h;	A 54% B n/a C n/a

vinyl acetate (108-05-4) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With lipase LIP In octane at 30℃; for 0.15h; Yields of byproduct given;	A n/a B n/a C 46%
With 4 Anstroem molecular sives; lipase LIP In di-isopropyl ether at 30℃; for 4h; Yields of byproduct given;	A n/a B n/a C 36%
In di-isopropyl ether at 35℃; for 0.666667h; Kinetics; Reagent/catalyst; Solvent; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C 21.1%
With Burkholderia cepacia lipase; C36H73O14S(1-)*C7H10N(1+) at 35℃; for 2.33333h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C 12%
With IL1; Lipase PS-C In di-isopropyl ether at 35℃; for 24h;	A n/a B n/a C 11%

1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8)

Conditions	Yield
With C46H34I4O6; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at -30℃; for 2h; Reagent/catalyst; Temperature; stereoselective reaction;	45%
With C45H32I4O6; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at -30℃; for 2h; stereoselective reaction;	45%

1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (S)-(-)-1-(naphthalen-1-yl)ethyl acetate (16197-94-7, 57573-90-7, 92697-21-7, 16197-95-8) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With vinyl acetate; Lipase PS In octane at 30℃; for 8h; Yields of byproduct given;	A 45% B n/a C n/a

vinyl acetate (108-05-4) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With Candida antarctica lipase B In 1,1,1,2-tetrafluoroethane at 25℃; for 72h; Resolution of racemate; Enzymatic reaction; optical yield given as %ee;	A n/a B 45%
With Candida antarctica lipase B In diethyl ether at 20℃; Enzymatic reaction;	A 33% B 33%
With 50 U aminoacylase E.C. 3.5.1.14 In hexane for 168h; Acetylation;	A n/a B 22%
With Novozyme 435 In toluene at 30℃; for 12h; Enzymatic reaction; Overall yield = 98.8%; Overall yield = 58.4 g;	A n/a B n/a

1'-naphthacetophenone (941-98-0) + Isopropenyl acetate (108-22-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
Stage #1: 1'-naphthacetophenone With aluminum oxide; sodium tetrahydroborate In hexane at 40℃; for 3h; Stage #2: Isopropenyl acetate With Lipase 'Amano' PS-C II In hexane at 25℃; for 12h;	A n/a B n/a C 42%

1-(1-naphthyl)ethanol (57605-95-5) → 1'-naphthacetophenone (941-98-0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8)

Conditions	Yield
With sodium hydrogencarbonate; sodium bromide; chiral azabicyclo-N-oxyl In dichloromethane at 0℃; Electrochemical reaction;	A 40% B n/a
With [palladium(II)((-)-sparteine)dibromide]; oxygen; caesium carbonate; (-)-sparteine In chloroform at 23℃; for 21h; Molecular sieve; optical yield given as %ee;

1-(1-naphthyl)ethanol (57605-95-5) + propionic acid anhydride (123-62-6) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (S)-1-(1-naphtnyl)ethyl propionate + (R)-1-(1-naphtnyl)ethyl propionate

Conditions	Yield
With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine In chloroform at 20 - 25℃; for 28h; optical yield given as %ee; enantioselective reaction;	A 39% B n/a C n/a
With (R)-7-chloro-2-phenyl-2,3-dihydroimidazo[1,2-a]quinoline; N-ethyl-N,N-diisopropylamine In chloroform at 0℃; for 8h;

1-(1-naphthyl)ethanol (57605-95-5) + propionic acid anhydride (123-62-6) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3) + (R)-1-(1-naphtnyl)ethyl propionate

Conditions	Yield
With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine In toluene at -40℃; for 1h; optical yield given as %ee; enantioselective reaction;	A 39% B n/a C n/a

ethene (74-85-1) + 1-Bromonaphthalene (90-11-9) + bis(pinacol)diborane (73183-34-3) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
Stage #1: ethene; 1-Bromonaphthalene; bis(pinacol)diborane With (1,2-dimethoxyethane)dichloronickel(II); (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; lithium methanolate In 1,4-dioxane at 30℃; for 20h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 25℃; Overall yield = 38 percent; Optical yield = 70 percent ee;	A n/a B 38%

Isopropenyl acetate (108-22-5) + 1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With Candida antarctica lipase B In diethyl ether at 20℃; Enzymatic reaction;	A 31% B 31%
With potassium phosphate; Novozym 435; (CO)2ClRu(benzyloxytetraphenylpentadienyl) In toluene at 25℃; for 20h;
With immobilized Candida antarctica Lipase B In diethyl ether at 20℃; for 30h;

1-ethylnapthelene (1127-76-0) → 1'-naphthacetophenone (941-98-0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With iodosylbenzene; iron(III) meso-tetraphenylporhinato chloride In dichloromethane at 0℃; for 1h; Yield given. Yields of byproduct given;

1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
hydrolysis of (+)-hydrogen phthalate salt;
Stage #1: 1-(1-naphthyl)ethanol With (R,R)-1,2-diphenylethylenediamine; cyclohexanone; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran at 60℃; for 4h; Stage #2: With hydrogen In tetrahydrofuran at 40℃; under 7500.6 Torr; for 16h; Title compound not separated from byproducts;
With MCCD-HPS packed column In hydrogenchloride; acetonitrile pH=8.6;

dimethyl zinc(II) (544-97-8) + 1-naphthaldehyde (66-77-3) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With tricarbonyl(η6-arene)chromium(0) complex derived from (1S,2R)-N,N-dibutylnorephedrine In hexane; toluene at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With (1S,2S,5R)-1-N,N-dimethylaminopropyl-2-isopropyl-5-methylcyclohexan-1-ol In diethyl ether for 160h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With Boc-(S)-CH(i-Pr)-CONHCH2CH2-(morpholin-4-yl) In hexane at 0℃; Title compound not separated from byproducts;

methylmagnesium chloride (676-58-4) + 1-naphthaldehyde (66-77-3) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With C9H21ClO3Ti*C9H18O2 In tetrahydrofuran Yield given. Yields of byproduct given;
Stage #1: methylmagnesium chloride With titanium(IV) isopropylate In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: 1-naphthaldehyde With (R)-3-(3,5-diphenylphenyl)-2,2'-dihydroxy-1,1'-binaphthyl In tetrahydrofuran; dichloromethane at 0℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; dichloromethane at 0℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

1-naphthaldehyde (66-77-3) + tetramethyl titanium (2371-70-2) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With isopropyl alcohol; trans-N-(1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzenesulfonamide Product distribution; 1.) ether, 30 min, -30 to -10 grad C, 2.) from -78 grad C to room temp., overnight; Further sulphonamide derivatives of norephedrine were investigated.;
With norephedrine mesitylsulphonamide; isopropyl alcohol 1.) ether, 30 min, -30 to -10 grad C, 2.) from -78 grad C to room temp., overnight; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1-naphthaldehyde (66-77-3) + C28H54O3Ti → (S)-1-(1-Naphthyl)ethanol (15914-84-8)

Conditions	Yield
at -60 - 20℃; for 3h;

C42H70O35*C12H10O (97150-89-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With sodium tetrahydroborate In solid for 120h; Product distribution; Ambient temperature; other variant: ultrasonic irradiation, 2 d;

1-(1-naphthyl)ethanol (57605-95-5) → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3) + 1-(naphthalen-1-yl)ethyl acetate (16197-95-8, 57573-90-7, 92697-21-7, 16197-94-7)

Conditions	Yield
With vinyl acetate; 4 Anstroem molecular sives; lipase LIP In di-isopropyl ether at 30℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1-(1-naphthyl)ethyl 4-nitrobenzoate → (S)-1-(1-Naphthyl)ethanol (15914-84-8) + (R)-1-(naphth-1-yl)ethanol (42177-25-3)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; methanol for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

N,N-diisopropylcarbamoyl chloride (19009-39-3) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) → (S)-N,N-diisopropyl O-[1-(1-naphthyl)]ethyl carbamate (1086338-60-4)

Conditions	Yield
Stage #1: (S)-1-(1-Naphthyl)ethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran; mineral oil at 20℃; for 48h; Inert atmosphere;	98%
With triethylamine In dichloromethane for 94h; Inert atmosphere; Reflux;	1.61 g

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 1-acetonaphthone 2,4-dinitrophenylhydrazone (5471-15-8)

Conditions	Yield
Stage #1: (S)-1-(1-Naphthyl)ethanol With peracetic acid; C9H17NO5S(1-)*C12H11IN(1+); acetic acid In 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 18h; Stage #2: (2,4-dinitro-phenyl)-hydrazine With sulfuric acid In diethyl ether; ethanol; water	95%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + (3S)-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyric acid (1315282-22-4) → (1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyrate (1315282-20-2)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; optical yield given as %de;	92%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) → 1'-naphthacetophenone (941-98-0)

Conditions	Yield
With 2-azaadamantane-N-oxyl; oxygen In aq. acetate buffer at 20℃; for 8h; pH=4.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; chemoselective reaction;	92%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) → (R)-α-methylnaphthyl azide

Conditions	Yield
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0 - 20℃; for 18h; Inert atmosphere;	92%

pentacarbonyl[(N,N-dimethylamino)(2-methyl-5-methoxycarbonylphenyl)carbene]chromium(0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) → pentacarbonyl[(N,N-dimethylamino)(3-(S)-1'-(1-naphthyl)ethoxycarbonyl-2-methylphenyl)carbene]chromium(0)

Conditions	Yield
With Na In neat (no solvent) naphthylethanol and Na were stirred under Ar at 100°C, finely powdered complex was added at 70°C, stirred for 30 min at 70°C and diminished pressure (1.5 kPa); dissolved in CH2Cl2, chromy. on silica gel column, hexane-CH2Cl2 1:1, asfoam, the mixt. of (S,S) and (R,S)-diastereomers;	85%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + (3S)-4-(1-methyl-1H-imidazolylcarbonyl)-3-phenylbutyric acid (1315282-23-5) → (1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-phenylbutyrate (1315282-21-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; optical yield given as %de;	85%

pentacarbonyl[(N,N-dimethylamino)(3-methoxycarbonyl-2-methylphenyl)carbene]chromium(0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) → pentacarbonyl[(N,N-dimethylamino)(3-(S)-1'-(1-naphthyl)ethoxycarbonyl-2-methylphenyl)carbene]chromium(0)

Conditions	Yield
With Na In neat (no solvent) naphthylethanol and Na were stirred under Ar at 100°C, finely powdered complex was added at 70°C, stirred for 30 min at 70°C and diminished pressure (1.5 kPa); dissolved in CH2Cl2, chromy. on silica gel column, hexane-CH2Cl2 1:1, asfoam, the mixt. of (S,S) and (R,S)-diastereomers;	83%

pentacarbonyl[(N,N-dimethylamino)(2-isopropyl-5-methoxycarbonylphenyl)carbene]chromium(0) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) → pentacarbonyl[(N,N-dimethylamino)(2-isopropyl-5-(S)-1'-(1-naphthyl)ethoxycarbonylphenyl)carbene]chromium(0)

Conditions	Yield
With Na In neat (no solvent) naphthylethanol and Na were stirred under Ar at 100°C, finely powdered complex was added at 70°C, stirred for 2 h at 70°C and diminished pressure (1.5 kPa); dissolved in CH2Cl2, chromy. on silica gel column, hexane-CH2Cl2 1:1, asfoam, the mixt. of (S,S) and (R,S)-diastereomers;	83%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + pivaloyl chloride (3282-30-2) → (S)-1-(naphthalen-1-yl)ethyl pivalate (1424035-88-0)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 12h;	81%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + (1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride (109216-50-4) → (1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (S)-1-naphthalen-1-yl-ethyl ester

Conditions	Yield
	70%

(S)-1-(1-Naphthyl)ethanol (15914-84-8) + 1-Phenyl-2-propyn-1-ol (4187-87-5) → 1-[(S)-1-(1-Phenyl-prop-2-ynyloxy)-ethyl]-naphthalene

Conditions	Yield
With ammonium tetrafluoroborate; [(Cp*)RuCl(SMe)]2 In 1,2-dichloro-ethane at 60℃; for 1h;	64%

4-carbethoxypiperidine (1126-09-6) + (S)-1-(1-Naphthyl)ethanol (15914-84-8) → ethyl (R)-1-(1-(naphthalen-1-yl)ethyl)piperidine-4-carboxylate

Conditions	Yield
Stage #1: (S)-1-(1-Naphthyl)ethanol With N-ethyl-N,N-diisopropylamine; Methanesulfonic anhydride In dichloromethane at 0℃; for 0.666667h; Stage #2: 4-carbethoxypiperidine In dichloromethane at 20℃; for 16h;	54%

Upstream product

• 57392-44-6 2,2,2-trichloroethyl butyrate 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 108-05-4 vinyl acetate 
• 108-24-7 acetic anhydride 
• 826-74-4 1-vinylnaphthalene 
• 3377-92-2 vinyl pivalate 
• 108-22-5 Isopropenyl acetate 
• 105-38-4 vinyl propionate 
• 93-08-3 methyl 2-naphthyl ketone 
• 123-62-6 propionic acid anhydride 
• 1402034-43-8 4,4,5,5-tetramethyl-2-(1-(naphthalen-1-yl)ethyl)-1,3,2-dioxaborolane 
• 75-16-1 methylmagnesium bromide 
• 66-77-3 1-naphthaldehyde 
• 818-44-0 vinyl octanoate 

Downstream Products

• 42177-25-3 (R)-1-(naphth-1-yl)ethanol 
• 1581755-39-6 (R)-N-(3-acetamidobenzyl)-1-(1-(naphthalen-1-yl)ethyl)-piperidine-4-carboxamide 
• 1581755-45-4 (R)-N-(3-fluorobenzyl)-1-(1-(naphthalen-1-yl)ethyl)-piperidine-4-carboxamide 
• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 226256-56-0 cinacalcet 
• 941-98-0 1'-naphthacetophenone 
• 5471-15-8 1-acetonaphthone 2,4-dinitrophenylhydrazone 
• 1315282-21-3 (1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-phenylbutyrate 
• 1315282-20-2 (1'S,3S)-1'-naphthylethyl-4-(1-methyl-1H-imidazolylcarbonyl)-3-(4-bromophenyl)butyrate 

Relevant articles and documents

Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition-Metal Catalysts

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Ferrocene derivative metal organic complex as well as preparation method and application thereof

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PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols

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