CAS No.64726-91-6,(R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one Suppliers

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Basic Information

Molecular Structure:
CAS No.:	64726-91-6
Name:	(R,Z)-5-(1-decenyl)dihydrofuran-2(3H)-one
Article Data:	19

Formula:	C₁₄H₂₄O₂
Molecular Weight:	224.343
Synonyms:	2(3H)-Furanone,5-(1-decenyl)dihydro-, [R-(Z)]-;2(3H)-Furanone, 5-(1Z)-1-decenyldihydro-,(5R)- (9CI);(-)-(R)-(5Z)-Tetradecenolide;(R)-(+)-5-[(Z)-Dec-1-enyl]dihydrofuran-2(3H)-one;(R)-Japonilure;(R,Z)-5-(-)-(Dec-1-enyl)oxacyclopentan-2-one;(R,Z)-5-(1-Decenyl)dihydro-2(3H)-furanone;(R,Z)-5-(Dec-1-enyl)oxacyclopentan-2-one;IN 60;IN 60 (pheromone);Japonilure;
EINECS:	265-035-8
Density:	0.985 g/cm³
Boiling Point:	340.3 °C at 760 mmHg
Flash Point:	141.3 °C
PSA:	26.30000
LogP:	3.99880

Synthetic route

: 72151-69-0
(R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one

: 64726-91-6
japonilure

Conditions

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

: 64726-91-6
japonilure

Conditions

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

: 64726-91-6
japonilure

Conditions

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

: 70606-00-7
(R)-tetrahydro-5-oxo-2-furancarbaldehyde

: nonyl(triphenyl)phosphonium bromide

: 64726-91-6
japonilure

Conditions

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;

: 64726-93-8
(S)-5-<(Z)-dec-1-enyl>dihydrofuran-2(3H)-one

: 64726-91-6
japonilure

Conditions

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;

: 397300-95-7
(5S)-1-pentadecen-6-yn-5-ol

: 64726-91-6
japonilure

Conditions

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

: 397300-89-9
(1R)-1-(3-butenyl)-2-undecynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

: 64726-91-6
japonilure

Conditions

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

: 764-93-2
1-decyne

: 64726-91-6
japonilure

Conditions

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

: 325141-84-2
(R)-[1,1-dimethylethyl-4-hydroxy-5-tetradecynoate]

: 64726-91-6
japonilure

Conditions

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

: 325141-83-1
[2(1'R),4R,5R]-2-[2-[[(1,1-dimethylethyl)oxy]carbonyl]-1-(1-decynyl)propyl]-4,5-dicyclohexyl-1,3,2-dioxaborolane

: 64726-91-6
japonilure

Conditions

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

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Specification

The Japonilure, with the cas registry number 64726-91-6, has the systematic name of (5R)-5-[(1Z)-dec-1-en-1-yl]dihydrofuran-2(3H)-one. And the molecular fomula of the chemical is C₁₄H₂₄O₂.

The characteristics of this chemical are as followings: (1)ACD/LogP: 4.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.21; (4)ACD/LogD (pH 7.4): 4.21; (5)ACD/BCF (pH 5.5): 938; (6)ACD/BCF (pH 7.4): 938; (7)ACD/KOC (pH 5.5): 4667.71; (8)ACD/KOC (pH 7.4): 4667.71; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.512; (14)Molar Refractivity: 68.35 cm³; (15)Molar Volume: 227.6 cm³; (16)Polarizability: 27.09×10^-24cm³; (17)Surface Tension: 39.9 dyne/cm; (18)Density: 0.985 g/cm³; (19)Flash Point: 141.3 °C; (20)Enthalpy of Vaporization: 58.39 kJ/mol; (21)Boiling Point: 340.3 °C at 760 mmHg; (22)Vapour Pressure: 8.67E-05 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C1O[C@@H](\C=C/CCCCCCCC)CC1
(2)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
(3)InChIKey: QTGIYXFCSKXKMO-XPSMFNQNBJ