64726-91-6

Basic information

• Product Name: (R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one
• Synonyms: (R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one;JAPONLURE;Japonilure;NURANONE;(5R)-5α-[(Z)-1-Decenyl]-4,5-dihydrofuran-2(3H)-one;(R)-5-[(Z)-1-Decenyl]dihydro-2(3H)-furanone;(R)-Japonilure;[5R,(-)]-5-((Z)-1-Decenyl)-4,5-dihydrofuran-2(3H)-one
• CAS NO: 64726-91-6
• Molecular Formula: C₁₄H₂₄O₂
• Molecular Weight: 224.33916
• EINECS: 265-035-8
• Mol File: 64726-91-6.mol
• Article Data: 19

Chemical Properties

• Boiling Point: bp0.1mm 130-134°
• Flash Point: 141.3 °C
• Appearance: /
• Density: 0.985 g/cm³
• Vapor Pressure: 8.67E-05mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: (R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one(64726-91-6)
• EPA Substance Registry System: (R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one(64726-91-6)

Safety Data

• Hazardous Substances Data: 64726-91-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4977, 1987 DOI: 10.1016/S0040-4039(00)96674-7

InChI:InChI=1/C14H24O2/c1-2-3-4-5-6-7-8-9-10-13-11-12-14(15)16-13/h9-10,13H,2-8,11-12H2,1H3/b10-9-/t13-/m0/s1

Synthetic route

(R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one (72151-69-0) → japonilure (64726-91-6)

Conditions	Yield
With quinoline; hydrogen; Lindlar's catalyst In pentane at 0℃; for 4h;	94%
With quinoline; hydrogen; Lindlar's catalyst In pentane at 0℃; for 5h;	91%
With quinoline; hydrogen; palladium on activated charcoal In pentane at 0℃; for 5h;	91%

(R,Z)-methyl 4-hydroxytetradec-5-enoate → japonilure (64726-91-6)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0 - 25℃; Inert atmosphere;	80%

(R)-((Z)-5-Dec-1-enyl)-tetrahydro-furan-2-ol → japonilure (64726-91-6)

Conditions	Yield
With pyridine; chromium(VI) oxide In dichloromethane for 2h; Ambient temperature;	30%

(R)-tetrahydro-5-oxo-2-furancarbaldehyde (70606-00-7) + nonyl(triphenyl)phosphonium bromide → japonilure (64726-91-6)

Conditions	Yield
With sodium methylsulfinylmethanide 1.) THF, 0 deg C, 1 h, 2a.) DMF, -40 deg C, 2 h, 2b.) RT, overnight; Yield given. Multistep reaction;

(S)-5-<(Z)-dec-1-enyl>dihydrofuran-2(3H)-one (64726-93-8) → japonilure (64726-91-6)

Conditions	Yield
With potassium hydroxide; triphenylphosphine; diethylazodicarboxylate 1.) MeOH, 60 deg C, 3 h, 2.) THF, 20 deg C, 13 h; Yield given. Multistep reaction;
With potassium hydroxide; triphenylphosphine; diethylazodicarboxylate 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h; Yield given. Multistep reaction;

(5S)-1-pentadecen-6-yn-5-ol (397300-95-7) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ozone / CH2Cl2 / 0.42 h / -78 °C 1.2: PPh3 / CH2Cl2 / 2 h / -78 °C 1.3: 86 percent / N-iodosuccinimide; N-tetrabutylammonium iodide / CH2Cl2 / 0.25 h / 20 °C 2.1: 94 percent / H2; quinoine / Lindlar catalyst / pentane / 4 h / 0 °C View Scheme

(1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (397300-89-9) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: MeSO3H / methanol / 8 h / Heating 1.2: 89 percent / Ba(OH)2*8H2O / methanol / 2 h / Heating 2.1: ozone / CH2Cl2 / 0.42 h / -78 °C 2.2: PPh3 / CH2Cl2 / 2 h / -78 °C 2.3: 86 percent / N-iodosuccinimide; N-tetrabutylammonium iodide / CH2Cl2 / 0.25 h / 20 °C 3.1: 94 percent / H2; quinoine / Lindlar catalyst / pentane / 4 h / 0 °C View Scheme

1-decyne (764-93-2) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 0.25 h / -78 °C 1.2: 97 percent / tetrahydrofuran / 18 h / 20 - 25 °C 2.1: 89 percent / hydrogen peroxide; aq. sodium hydroxide / diethyl ether / 2 h / 25 °C 3.1: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 4.1: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme
Multi-step reaction with 4 steps 1: 86.2 percent / n-butyllithium / tetrahydrofuran / 15 h / 1.) 3 deg C, 1 h, 2.) -50 deg C to r.t., 15 h 2: 70.1 percent / AlCl3 / CH2Cl2 / 1.) -65 deg C, 2.5 h, then -40 deg C, 1 h, 2.) -30 deg C, 2 h, then -30 deg C to 0 deg C, 15 h 3: Chirald, LiAlH4 / diethyl ether / 1.) -100 deg C, 2 h, 2.) -70 to -65 deg C, 2 h 4: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme
Multi-step reaction with 8 steps 1: 1.) ethylmagnesium bromide / 1.) THF, r.t., 1 h, 2.) THF, 5 deg C, 2 h 2: 88 percent / aq. NaIO4 / diethyl ether / 2 h / Ambient temperature 3: 94 percent / silver carbonate on celite (Fetizon's reagent) / benzene / 8.5 h / Heating 4: 89 percent / 90percent trifluoroacetic acid / 0.25 h / Ambient temperature 5: 74.6 percent / H2 / Pb poisoned 5percent Pd/CaCO3 (Lindlar catalyst) / ethanol 6: 770 mg / conc. H2SO4 / 0.25 h / Ambient temperature 7: 1.21 g / acetic anhydride, acetic acid / Heating 8: 1.) CuI, LiI, TMSCl, 2.) n-Bu3SnH / 1.) THF, -60 deg C, 10 min, 2.) up to 0 deg C, 30 min View Scheme
Multi-step reaction with 3 steps 1: Mg / tetrahydrofuran / 1 h / Heating 2: 68 percent / tetrahydrofuran / -65 deg C, 3 h -> room temperature, 20 h 3: 1.) 9-BBN, (+)-α-pinene, 2.) 2-hydroxyethylamine, 3.) NaH, 4.) H2 / 4.) Pd on CaCO3 View Scheme
Multi-step reaction with 3 steps 1: 85 percent / CuBr-(CH3)2S 2: 1.) Alpine-borane, 2.) NaOH/MeOH / 1.) room temp., 7 d, 2.) reflux, 15 min 3: H2 / Pd/CaCO3 poisoned with lead/quinoline View Scheme

(R)-[1,1-dimethylethyl-4-hydroxy-5-tetradecynoate] (325141-84-2) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 2: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme

[2(1'R),4R,5R]-2-[2-[[(1,1-dimethylethyl)oxy]carbonyl]-1-(1-decynyl)propyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane (325141-83-1) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / hydrogen peroxide; aq. sodium hydroxide / diethyl ether / 2 h / 25 °C 2: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 3: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme

(2R,5R)-2-((Z)-Dec-1-enyl)-5-methoxy-tetrahydro-furan (173464-16-9) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / aq. HCl / tetrahydrofuran / 3 h / 55 - 60 °C 2: 30 percent / CrO3, pyridine / CH2Cl2 / 2 h / Ambient temperature View Scheme

Methyl 3,5,6-trideoxy-2-O-methanesulfonyl-α-L-threo-tetradec-5-(Z)-eno-furanoside (173464-14-7) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 43 percent / NaBH4 / hexamethylphosphoric acid triamide / 24 h / 100 °C 2: 76 percent / aq. HCl / tetrahydrofuran / 3 h / 55 - 60 °C 3: 30 percent / CrO3, pyridine / CH2Cl2 / 2 h / Ambient temperature View Scheme

Methyl 3,5,6-trideoxy-L-threo-tetradec-5-(Z)-eno-furanoside → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 51 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature 2: 43 percent / NaBH4 / hexamethylphosphoric acid triamide / 24 h / 100 °C 3: 76 percent / aq. HCl / tetrahydrofuran / 3 h / 55 - 60 °C 4: 30 percent / CrO3, pyridine / CH2Cl2 / 2 h / Ambient temperature View Scheme

1-decynyltrimethylsilane (54559-17-0) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70.1 percent / AlCl3 / CH2Cl2 / 1.) -65 deg C, 2.5 h, then -40 deg C, 1 h, 2.) -30 deg C, 2 h, then -30 deg C to 0 deg C, 15 h 2: Chirald, LiAlH4 / diethyl ether / 1.) -100 deg C, 2 h, 2.) -70 to -65 deg C, 2 h 3: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme

Methyl 4-Oxo-5-tetradecynoate (77889-02-2) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Chirald, LiAlH4 / diethyl ether / 1.) -100 deg C, 2 h, 2.) -70 to -65 deg C, 2 h 2: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 1.) Alpine-borane, 2.) NaOH/MeOH / 1.) room temp., 7 d, 2.) reflux, 15 min 2: H2 / Pd/CaCO3 poisoned with lead/quinoline View Scheme
Multi-step reaction with 3 steps 1: 1.) lithium aluminum hydride, R-2,2'-dihydroxy-1,1'-binaphthyl, CH3OH / 1.) THF, room temperature, 2.) -100 deg C, 1 h and -78 deg C, 2 h 2: p-toluenesulfonic acid / benzene / 1 h / Heating 3: 90 percent / Lindlar cat. View Scheme

methyl (RS)-4-hydroxy-5-tetradecynoate (78685-94-6) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH / methanol / 0.25 h / Heating 2: 0.5 h / 120 °C / 0.2 Torr 3: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: 83 percent / pyridine 2: 41 percent / 24 h / 25 °C / lipase OF, phosphate buffer, pH 7 3: 91 percent / H2, quinoline / Lindlar catalyst / pentane / 5 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: 41 percent / diisopropyl ether / 48 h / Ambient temperature; lipase PS 2: 83 percent / 23 h / 25 °C / lipase OF, phosphate buffer, pH 7 3: 91 percent / H2, quinoline / Lindlar catalyst / pentane / 5 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: 43 percent / diisopropyl ether / 30 h / Ambient temperature; lipase PS 2: 81 percent / 5percent KOH, methanol / 0.25 h / Heating 3: 91 percent / H2, quinoline / Lindlar catalyst / pentane / 5 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 88 percent / pyridine 2: 43 percent / H2O / 16 h / 25 °C / palatase A, phosphate buffer, pH 7 3: 80 percent / diisopropyl ether / 10 h / Ambient temperature; lipase PS 4: 81 percent / 5percent KOH, methanol / 0.25 h / Heating 5: 91 percent / H2, quinoline / Lindlar catalyst / pentane / 5 h / 0 °C View Scheme

(4R,5S,6R)-5,6-dihydroxy-tetradecan-4-olide (111192-37-1) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / p-TsOH / CH2Cl2 / 0.5 h / Ambient temperature 2: 2) aq. sodium acetate / 1) acetic anhydride, reflux, 140 deg C, 1.5 h; 2) H2O, 4 h, 10 deg C View Scheme

(R)-4-hydroxy-5-tetradecynoic acid (88939-18-8) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / 120 °C / 0.2 Torr 2: 71.7 percent / H2, quinoline / 5percent Pd/CaCO3 / pentane / 1 h / 0 °C View Scheme

(4R,5S,6R)-ethyl-4-benzyloxy-5,6-(isopropylidenedioxy)-2,7-tetradecadienate → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) H2; 2) 90 percent aq. CF3COOH / 1) Pd-black / 1) 5 percent CH3COOH/MeOH, RT, 4-6 h; 2) H2O, RT, 3 h 2: 90 percent / p-TsOH / CH2Cl2 / 0.5 h / Ambient temperature 3: 2) aq. sodium acetate / 1) acetic anhydride, reflux, 140 deg C, 1.5 h; 2) H2O, 4 h, 10 deg C View Scheme

(2S,3R,4S,5Z)-2,3-dihydroxy-5-tetradecen-4-olide (147618-20-0) → japonilure (64726-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 770 mg / conc. H2SO4 / 0.25 h / Ambient temperature 2: 1.21 g / acetic anhydride, acetic acid / Heating 3: 1.) CuI, LiI, TMSCl, 2.) n-Bu3SnH / 1.) THF, -60 deg C, 10 min, 2.) up to 0 deg C, 30 min View Scheme

japonilure (64726-91-6) → (4R,5Z)-5-tetradecene-1,4-diol (105676-77-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature;

japonilure (64726-91-6) → (Z)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tetradec-5-en-4-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 2 h View Scheme

japonilure (64726-91-6) → (4R,5Z)-1-t-butyldimethylsilyloxy-5-tetradecene-1-yl benzoate

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 2 h 3: pyridine / 1 h / Ambient temperature View Scheme

japonilure (64726-91-6) → (4R,5Z)-5-tetradecene-1,4-diyl dibenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: pyridine / 1 h / Ambient temperature View Scheme

Upstream product

• 77889-02-2 methyl 4-oxo-5-tetradecyonate 
• 128657-75-0 4-Hydroxy-tetradec-5-ynoic acid 
• 72151-69-0 (R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one 
• 111-83-1 1-bromo-octane 
• 34683-71-1 undec-2-yn-1-ol 
• 104178-29-2 undec-2-ynal 
• 77889-07-7 (R)-methyl 4-hydroxy-5-tetradecyn-4-olide 
• 81793-47-7 1-methoxycarbonyltridec-4-ol-5-ynyl monophthalate 
• 52713-82-3 dec-1-yn-1-ylmagnesium bromide 
• 147618-16-4 (2S,3R,4S,5S)-2,5-dihydroxy-3,4-isopropylidenedioxy-pentadec-6-yn-1-ol 
• 147618-19-7 (2S,3R,4S)-2,3-dihydroxy-5-tetradecyn-4-olide 
• 147618-20-0 (2S,3R,4S,5Z)-2,3-dihydroxy-5-tetradecen-4-olide 
• 88939-18-8 (R)-4-hydroxy-5-tetradecynoic acid 
• 111192-37-1 (4R,5S,6R)-5,6-dihydroxy-tetradecan-4-olide 

Relevant articles and documents

Asymmetric Synthesis of γ-Lactones. A Facile Synthesis of the Sex Pheromone of the Japanese Beetle

The sex pheromone of the Japanese beetle, (R)-(-)-(Z)-5-tetradecen-4-olide, has been prepared in essentially 100percent optical purity by using the asymmetric reducing agent B-3-pinanyl-9-borabicyclononane to introduce chirality.

Convergent and enantioselective syntheses of both enantiomers of (5Z)-tetradecen-4-olide, scarab beetle pheromones

Japonilure and its enantiomer, that is, (R)-(-)- and (S)-(+)-(5Z)-tetradecen-4-olide, have been synthesised in satisfactory overall yields using a highly convergent procedure. In situ prepared 1-decynylethylzinc was enantioselectively coupled to isopropyl 4-oxobutanoate in the presence of (S)- or (R)-BINOL. The alkoxy-ester intermediates obtained were cyclised to the corresponding substituted γ-lactones, carrying a triple bond in the side chain. Lindlar-hydrogenation of the latter yielded the target compounds.

Synthesis of (R)-japonilure and (4R,9Z)-9-octadecen-4-olide, pheromones of the Japanese beetle and currant stem girdler

Asymmetric total synthesis of the sex pheromones of Japanese beetle and currant stem girdler, (R)-japonilure (1) and (4R,9Z)-9-octadecen-4-olide (2), has been achieved. Copyright Taylor & Francis Group, LLC.

Asymmetric synthesis of the Japanese beetle pheromone via boronic esters

The pheromone of the Japanese beetle, [R-(Z)]-5-(1-decenyl)dihydro-2(3H)-furanone (7), has been synthesized efficiently in high enantiomeric purity via 1,2-dicyclohexyl-1,2-ethanediol boronic esters. The synthetic route involves reaction of an α-chloro boronic ester with an alkynyllithium, and provides the first successful example of this substitution process in an asymmetric synthesis.