(R)-(-)-5-(dec-1-ynyl)-tetrahydrofuran-2-one
japonilure
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% |
japonilure
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 0 - 25℃; Inert atmosphere; | 80% |
japonilure
Conditions | Yield |
---|---|
With pyridine; chromium(VI) oxide In dichloromethane for 2h; Ambient temperature; | 30% |
(R)-tetrahydro-5-oxo-2-furancarbaldehyde
japonilure
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
japonilure
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
japonilure
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
japonilure
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
japonilure
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]
japonilure
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
japonilure
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
japonilure
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
japonilure
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 |
japonilure
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
japonilure
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
japonilure
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
japonilure
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
japonilure
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
japonilure
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 |
japonilure
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
japonilure
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
(4R,5Z)-5-tetradecene-1,4-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature; |
japonilure
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
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
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: pyridine / 1 h / Ambient temperature View Scheme |
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
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