cis-9-hexadecenoic acid
palmitoleyl alcohol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; | 98% |
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 24h; | 97% |
Multi-step reaction with 2 steps 1: 0.19 g / conc. H2SO4 / 6 h / Heating 2: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme |
9-hexadecyn-1-ol
palmitoleyl alcohol
Conditions | Yield |
---|---|
With hydrogen; ethylendiamine poisoned P-2 Ni In ethanol | 97% |
With hydrogen; Ni-P2 | 88% |
With bis(cyclopentadienyl)titanium dichloride; di-iso-butylmagnesium; ammonium chloride 1.) Et2O, 20 deg C, 30 min, 2.) H2O; Yield given. Multistep reaction; |
(Z)-9-hexadecenoic acid methyl ester
palmitoleyl alcohol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 5h; | 96% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; | 92% |
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Ambient temperature; | 0.14 g |
With lithium aluminium tetrahydride In diethyl ether for 2h; Reflux; | 2.3 g |
9-tetradecyn-1-ol
palmitoleyl alcohol
Conditions | Yield |
---|---|
With hydrogen; P2Ni | 86% |
(Z)-hexadec-9-en-1-yl acetate
palmitoleyl alcohol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 5h; | 82% |
With sodium hydroxide In methanol |
palmitoleyl alcohol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 3h; | 82% |
heptanal
(9-hydroxynonyl)(triphenyl)phosphonium bromide
A
trans-hexadec-9-en-1-ol
B
palmitoleyl alcohol
Conditions | Yield |
---|---|
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
palmitoleyl alcohol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol; water at 20℃; for 15h; Yield given; |
2-[((Z)-Hexadec-9-enyl)oxy]-tetrahydro-pyran
palmitoleyl alcohol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 3h; Heating; Yield given; | |
With toluene-4-sulfonic acid In methanol at 20℃; for 16h; |
(Z)-4-undecene-1-ol
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 2: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 3: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 82 percent / PBr3, pyridine / diethyl ether / 1) rt, overnight, 2) reflux, 2 h 2: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 3: p-toluenesulphonic acid / methanol / 3 h / Heating View Scheme |
(Z)-4-undecenal
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme |
(Z)-4-undecenyl bromide
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 2: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight 2: p-toluenesulphonic acid / methanol / 3 h / Heating View Scheme |
1,1-dimethoxy-8-tosyloxy-(4Z)-octene
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h 2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme |
1,1-dimethoxy-(4Z)-undecene
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 3.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme |
methyl ester of azelaic acid aldehyde
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 2: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / toluene / 4 h / Reflux 2: lithium aluminium tetrahydride / diethyl ether / 2 h / Reflux View Scheme |
triphenylheptylphosphonium bromide
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C View Scheme |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation 2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 4.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C View Scheme |
8-Bromo-1-octene
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 View Scheme |
1-octynyllithium
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 View Scheme |
hexadec-1-en-9-yne
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 88 percent / H2 / Ni-P2 View Scheme |
10,11-dibromo-undecanoic acid
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme |
10-undecenoic acid
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme |
9-undecynoic acid methyl ester
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme |
(Z)-0-undecenoic acid methyl ester
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 84 percent / O3 / CH2Cl2 / -78 °C 2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 3: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C View Scheme |
2-(8-bromooctyloxy)tetrahydropyran
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme | |
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 1.2: 16 h / Reflux 2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme |
1,8-Octanediol
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 75 percent / 48percent HBr / Heating 2: 99 percent / p-toluenesulfonic acid 3: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 4: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 5: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme |
8-bromooctanol
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 99 percent / p-toluenesulfonic acid 2: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 3: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 4: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme | |
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 2.2: 16 h / Reflux 3.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 4.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme |
1-tetrahydropyranyloxy-n-9-hexadecyn
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 2: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C View Scheme |
palmitoleyl alcohol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; | 98% |
With pyridinium chlorochromate In dichloromethane for 1.5h; Ambient temperature; | 94% |
With pyridinium chlorochromate | 94% |
palmitoleyl alcohol
(Z)-hexadec-9-enyl bromide
Conditions | Yield |
---|---|
With bromine; triphenylphosphine In benzene at 20℃; for 3h; | 97% |
With carbon tetrabromide; triphenylphosphine In dichloromethane for 16h; Ambient temperature; | 94% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 16h; | 94% |
palmitoleyl alcohol
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In toluene at 20℃; for 3h; | 89% |
Conditions | Yield |
---|---|
With pyridine for 1h; Ambient temperature; | 85% |
With pyridine for 24h; Ambient temperature; | 68% |
With pyridine for 25h; Ambient temperature; | 0.1 g |
In pyridine at 20℃; for 24h; | 1.4 g |
cholesteryl p-toluenesulfonate
palmitoleyl alcohol
cholesteryl cis-9'-hexadecenyl ether
Conditions | Yield |
---|---|
at 110℃; for 2.5h; | 54.1% |
palmitoleyl alcohol
methanesulfonyl chloride
palmitoleyl methanesulfonate
Conditions | Yield |
---|---|
With pyridine | |
With pyridine at 0 - 20℃; for 24h; |
methanol
palmitoleyl alcohol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction; |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C View Scheme |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C View Scheme |
palmitoleyl alcohol
(3S,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-8aH-benzo[1,4]dioxine-2,6-dione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C 4.1: 93 percent / ZnBr; CH3NO2 / 20 °C 5.1: 55 percent / PhIOTMS(OTf); TMSOTf / CH2Cl2 / 0.25 h / 0 °C View Scheme |
palmitoleyl alcohol
2-(2-bromo-6-heptadec-10-enyl-3-hydroxy-phenoxy)-N-methoxy-N-methyl-propionamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C 4.1: 93 percent / ZnBr; CH3NO2 / 20 °C View Scheme |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C View Scheme |
palmitoleyl alcohol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C 2.1: Mg / tetrahydrofuran / 4 h / Heating 2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C 3.1: 90 percent / HCl / dioxane / 1.25 h / 80 °C View Scheme |
The 9-Hexadecen-1-ol, (9Z)-, with the CAS registry number 10378-01-5, is also known as cis-9-Hexadecenol. Its EINECS registry number is 233-831-4. This chemical's molecular formula is C16H32O and molecular weight is 240.42. Its IUPAC name is called (Z)-hexadec-9-en-1-ol.
Physical properties of 9-Hexadecen-1-ol, (9Z)-: (1)ACD/LogP: 6.73; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 14; (6)Index of Refraction: 1.46; (7)Molar Refractivity: 77.76 cm3; (8)Molar Volume: 283.7 cm3; (9)Surface Tension: 31.5 dyne/cm; (10)Density: 0.847 g/cm3; (11)Flash Point: 115.4 °C; (12)Enthalpy of Vaporization: 67.6 kJ/mol; (13)Boiling Point: 340 °C at 760 mmHg; (14)Vapour Pressure: 5.88E-06 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCCC=CCCCCCCCCO
(2)Isomeric SMILES: CCCCCC/C=C\CCCCCCCCO
(3)InChI: InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h7-8,17H,2-6,9-16H2,1H3/b8-7-
(4)InChIKey: LBIYNOAMNIKVKF-FPLPWBNLSA-N
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