Conditions | Yield |
---|---|
With monoammonium 12-tungstophosphate for 12h; Heating; | 100% |
With sulfuric acid In methanol for 6h; Reflux; | 100% |
Stage #1: methanol; 10-undecenoic acid With thionyl chloride at 10 - 20℃; for 12h; Stage #2: With potassium carbonate In water pH=> 9; | 99% |
Conditions | Yield |
---|---|
In methanol at 0 - 20℃; for 6h; | 100% |
Conditions | Yield |
---|---|
98% | |
In dichloromethane at 20℃; for 1h; Inert atmosphere; | 92% |
With potassium carbonate | 87% |
Conditions | Yield |
---|---|
Stage #1: 4-quinolylmethyl undec-10-enoate With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 50℃; for 12h; Reduction; Deprotection; Stage #2: methyl iodide With sodium carbonate In water; dimethyl sulfoxide at 20℃; for 12h; Methylation; | 95% |
Conditions | Yield |
---|---|
With Amberlyst 15 at 60℃; for 48h; | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide Inert atmosphere; Reflux; | 93% |
With sodium hydroxide for 48h; Reflux; | 93% |
Conditions | Yield |
---|---|
With sulfuric acid for 4h; Inert atmosphere; Reflux; | 92% |
Methyl 10-undecenoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 6h; Heating; | 90% |
11-tert-Butylperoxy-11-methoxy-undec-1-ene
Methyl 10-undecenoate
Conditions | Yield |
---|---|
In methanol at 60℃; | 89% |
methyl 11-(benzo[d]thiazol-2-ylsulfonyl)-10-hydroxyundecanoate
Methyl 10-undecenoate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 17h; | 89% |
Conditions | Yield |
---|---|
With copper(II)-citrate; hexamethylenetetramine; hypophosphorous acid In water; N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction; | 84% |
Conditions | Yield |
---|---|
With Oxone at 20℃; for 4h; oxidative esterification; | 81% |
Conditions | Yield |
---|---|
With iodine; potassium carbonate for 20h; Heating; | 75% |
Conditions | Yield |
---|---|
With sodium hypochlorite; tetrabutylammomium bromide In ethyl acetate at 20℃; for 2.85h; | 75% |
methanol
C12H21F5O2Si(2-)*2K(1+)
A
Methyl 10-undecenoate
B
(E)-11-Methoxy-undec-10-enoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; copper diacetate for 21h; Ambient temperature; | A 16% B 67% |
Conditions | Yield |
---|---|
With pyridine; copper (II) carbonate hydroxide at 90℃; for 24h; Chan-Lam Coupling; | 60% |
12-methoxy-12-oxododecanoic acid
A
methyl undecanoate
B
Methyl 10-undecenoate
C
docosanedioic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium methanolate In methanol at 40 - 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.25 F mol-1; cell voltage 40-70 V; Yield given; | A n/a B n/a C 53% |
With potassium methanolate In methanol at 40 - 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.25 F mol-1; cell voltage 40-70 V; Yields of byproduct given; | A n/a B n/a C 53% |
Conditions | Yield |
---|---|
With sand for 0.75h; | A n/a B 49% |
Conditions | Yield |
---|---|
With Pt/HCl/F-ZSM-5 In water at 350 - 480℃; Reagent/catalyst; Temperature; | A 26.4% B 48.3% |
at 120 - 170℃; under 145 Torr; Die Spaltung verlaeuft fast quantitativ, wenn ueber mit Borax getraenktem Bimstein destilliert wird; | |
at 550℃; |
methyl 11-bromo-10-hydroxyundecanoate
A
Methyl 10-undecenoate
B
(+/-)-10-Hydroxyundecansaeure-methylester
C
methyl 10-oxoundecanoate
D
methyl 8-undecenoate
Conditions | Yield |
---|---|
With chlorotris(triphenylphosphine)cobalt(I) for 6h; Ambient temperature; Yield given. Further byproducts given; | A n/a B 42% C 44% D n/a |
methyl 11-bromo-10-hydroxyundecanoate
A
Methyl 10-undecenoate
B
(+/-)-10-Hydroxyundecansaeure-methylester
C
methyl 10-oxoundecanoate
D
methyl 8-undecenote
Conditions | Yield |
---|---|
With chlorotris(triphenylphosphine)cobalt(I) In benzene at 60℃; for 7.5h; Yield given; | A n/a B 42% C 44% D n/a |
(E)-2-hydroxyiminocyclododecanone
A
Methyl 10-undecenoate
B
(Z)-2-hydroxyiminocyclododecanone
C
12-hydroxybicyclo<8.2.0>dodecan-11-one oxime
D
(2-oxocyclodecane)acetonitrile
Conditions | Yield |
---|---|
In methanol at 28℃; for 4h; Irradiation; Yields of byproduct given; | A n/a B 18% C n/a D n/a |
In methanol at 28℃; for 12h; Irradiation; | A 13% B n/a C n/a D n/a |
In methanol at 28℃; for 12h; Irradiation; | A n/a B n/a C n/a D 5% |
In methanol at 28℃; for 6h; Irradiation; Yield given; |
(E)-2-hydroxyiminocyclododecanone
A
Methyl 10-undecenoate
B
(2-oxocyclodecane)acetonitrile
Conditions | Yield |
---|---|
In methanol for 12h; Irradiation; | A 13% B n/a |
In methanol for 12h; Irradiation; | A n/a B 5% |
Conditions | Yield |
---|---|
Destillation unter normalem Druck; ricinolic acid methyl ester; |
Methyl 10-undecenoate
Conditions | Yield |
---|---|
durch thermische Zersetzung; |
methyl ricinoleate
Methyl 10-undecenoate
Conditions | Yield |
---|---|
(methylation); | |
Multi-step reaction with 2 steps 1: PCl5 / benzene / Heating 2: 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Heating 2: 2 h / Reflux View Scheme |
12-Methylricinolsaeure-methylester
Methyl 10-undecenoate
Conditions | Yield |
---|---|
(pyrolysis); |
11-bromo-undecanoic acid methyl ester
A
Methyl 10-undecenoate
B
methyl (E) 9-undecenoate
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In tetrahydrofuran; hexane Product distribution; Mechanism; Ambient temperature; other halides; var. reagents; |
Methyl 10-undecenoate
10-oxo-decanoic acid methyl ester
Conditions | Yield |
---|---|
With 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine; oxygen In acetonitrile for 12h; Ambient temperature; Irradiation; | 100% |
With ozone; triphenylphosphine In methanol; dichloromethane at -78 - 20℃; for 6h; | 100% |
With sodium periodate; osmium(VIII) oxide; tetra(n-butyl)ammonium hydrogensulfate In water for 22h; Ambient temperature; | 97% |
Methyl 10-undecenoate
methyl 9-(oxiran-2-yl)nonanoate
Conditions | Yield |
---|---|
With Oxone; ethylene diamine tetraacetic acid tetrasodium salt; sodium hydrogencarbonate In acetonitrile at 0℃; for 1h; | 100% |
With dodecatungstophosphoric acid; dihydrogen peroxide; Aliquat 336 In chloroform at 65℃; for 5h; | 99% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 12h; | 93% |
Methyl 10-undecenoate
methyl 10-oxoundecanoate
Conditions | Yield |
---|---|
With oxygen; copper(l) chloride; palladium dichloride In tetrahydrofuran; water at 20℃; for 10h; | 100% |
With water; oxygen; copper(l) chloride In tetrahydrofuran at 20℃; under 759.826 Torr; for 36h; Wacker-Tsuji Olefin Oxidation; | 96% |
With tetraethylammonium chloride; oxygen; copper dichloride; palladium dichloride In N,N-dimethyl-formamide at 20℃; for 6h; Product distribution; other solvents, reagents, reagents ratios, temperature, times; | 95% |
Conditions | Yield |
---|---|
Stage #1: Methyl 10-undecenoate With water; sodium hydroxide Reflux; Stage #2: With hydrogenchloride In water | 100% |
Acidic conditions; | 44.8% |
Hydrolysis; |
Methyl 10-undecenoate
dimethyl cis-but-2-ene-1,4-dioate
A
dimethyl dodec-2-en-1,12-dioate
B
acrylic acid methyl ester
Conditions | Yield |
---|---|
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In toluene at 50℃; for 3h; Reagent/catalyst; Temperature; | A 100% B n/a |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 5h; | 99% |
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 6h; Autoclave; chemoselective reaction; | 98% |
With isopropyl alcohol In hexane at 0 - 20℃; for 0.25h; Bouveault-Blanc Reduction; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With magnesium nitride In methanol at 80℃; for 24h; | 99% |
With ammonia In methanol for 120h; | 48% |
Conditions | Yield |
---|---|
With C40H56N2RuSi4; hydrogen In toluene at 25℃; under 760.051 Torr; for 1.5h; Schlenk technique; | 99% |
With C40H56FeN2Si4(2-); hydrogen In 1,2-dimethoxyethane at 80℃; under 7600.51 Torr; for 2h; Schlenk technique; Autoclave; | 99% |
With hydrogen; palladium dichloride In dichloromethane at 20℃; under 760 Torr; | 98% |
Togni's reagent II
Methyl 10-undecenoate
(E)-methyl 12,12,12-trifluorododec-9-enoate
Conditions | Yield |
---|---|
With copper(l) chloride In methanol at 70℃; for 0.166667h; Sealed tube; Inert atmosphere; | 99% |
With tetrakis(actonitrile)copper(I) hexafluorophosphate In methanol at 0 - 20℃; for 23.25h; Inert atmosphere; optical yield given as %de; | 79% |
Conditions | Yield |
---|---|
With C20H22N2ORh(1+)*C24H20B(1-); hydrogen In toluene at 85℃; under 37503.8 Torr; for 6h; chemoselective reaction; | 99% |
Methyl 10-undecenoate
dimethyl 10-eicosenedioate
Conditions | Yield |
---|---|
With Grubbs catalyst first generation at 20 - 50℃; for 3h; | 98% |
With C29H36N3O4Ru In tetrahydrofuran at 35℃; for 12h; Inert atmosphere; | 94% |
With silica immobilized second generation Hoveyda-Grubbs catalyst In hexane at 59.84℃; for 5h; | 85% |
Methyl 10-undecenoate
methylmagnesium bromide
11-hydroxy-11-methyl-dodec-1-ene
Conditions | Yield |
---|---|
Stage #1: Methyl 10-undecenoate; methylmagnesium bromide In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; | 98% |
In tetrahydrofuran |
Conditions | Yield |
---|---|
With eosin; caesium carbonate In N,N-dimethyl acetamide at 20℃; for 48h; Inert atmosphere; Sealed tube; Irradiation; | 98% |
Methyl 10-undecenoate
methyl (E) 9-undecenoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 10h; Heating; | 97% |
Conditions | Yield |
---|---|
With dilauryl peroxide In neat (no solvent) at 85℃; Sealed tube; | 97% |
Methyl 10-undecenoate
1-amino-3-(dimethylamino)propane
N-[3-(dimethylamino)propyl]undec-10-enamide
Conditions | Yield |
---|---|
With sodium methylate at 150℃; for 4h; Reagent/catalyst; Temperature; | 96.3% |
Triethoxysilane
Methyl 10-undecenoate
11-triethoxysilanylundecanoic acid methyl ester
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 60℃; for 6h; | 96% |
dihydrogen hexachloroplatinate for 46h; Heating; |
Methyl 10-undecenoate
methyl difluoroiodoacetate
2,2-Difluoro-4-iodo-tridecanedioic acid dimethyl ester
Conditions | Yield |
---|---|
copper In N,N-dimethyl-formamide for 6h; Ambient temperature; | 96% |
Methyl 10-undecenoate
phenyl trifluoromethylsulfide
1,1,1-trifluoro-11-dodecen-2-one
Conditions | Yield |
---|---|
With Triethylgermyl-natrium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -60℃; for 1.5h; | 96% |
Methyl 10-undecenoate
[1',1'-2H2]-undec-10-en-1-ol
Conditions | Yield |
---|---|
With lithium aluminium deuteride In tetrahydrofuran at 0 - 25℃; | 96% |
With ethyl [2]alcohol; sodium In hexane; mineral oil at 0℃; for 0.0833333h; Inert atmosphere; | 95% |
With ethyl [2]alcohol; sodium In hexane; mineral oil at 0 - 20℃; for 0.166667h; Bouveault-Blanc Reduction; Inert atmosphere; | 95% |
Methyl 10-undecenoate
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
methyl 11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)undecanoate
Conditions | Yield |
---|---|
With trihexyltetradecylP(+) dodecylbenzene sulfonate; N-pentyl-4-methylpy 7,8-(Cy2P)2-7,8-nido-C2B9H10; Ir nanoparticles In dichloromethane (Ar); react. alkene with boron compd. in the presence of Ir nanoparticles and boronate in CH2Cl2 and trihexyltetradecylphosphonium dodecylbenzene sulfonate at room temp. for 12 h with stirring; evapn., extn. with Et2O, concn. in vac., chromy. (SiO2, hexane/Et2O 8:1 vol.); elem. anal.; | 96% |
With 1-hexyl-3-methylimidazolium triflate; N-pentyl-4-methylpy 7,8-(Cy2P)2-7,8-nido-C2B9H10; Ir nanoparticles In dichloromethane (Ar); react. alkene with boron compd. in the presence of Ir nanoparticles and boronate in CH2Cl2 and 1-hexyl-3-methylimidazolium trifluoromethanesulfonate at room temp. for 12 h with stirring; evapn., extn. with Et2O, concn. in vac., chromy. (SiO2, hexane/Et2O 8:1 vol.); | 93% |
With trihexyltetradecylP(+) dodecylbenzene sulfonate; catalyst: Ir/1,2-bis(diphenylphosphino)ethane In dichloromethane (Ar); react. alkene with boron compd. in the presence of Ir nanoparticles and diphosphine in CH2Cl2 and trihexyltetradecylphosphonium dodecylbenzene sulfonate at room temp. for 12 h with stirring; evapn., extn. with Et2O, concn. in vac., chromy. (SiO2, hexane/Et2O 8:1 vol.); | 88% |
With MesBIPCoCl2; sodium t-butanolate at 25℃; for 1h; | 70% |
With [(1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene)Fe(CO)4] In neat (no solvent) at 20℃; for 24h; Inert atmosphere; UV-irradiation; Schlenk technique; regioselective reaction; | 52% |
iodotrifluoromethane
Methyl 10-undecenoate
methyl 12,12,12-trifluoro-10-iodododecanoate
Conditions | Yield |
---|---|
With Raney Ni (W-2) In methanol at 80℃; for 20h; Addition; | 95% |
With triethyl borane In hexane at -24℃; for 3.5h; | 86% |
Methyl 10-undecenoate
2-hydroxyethanethiol
methyl 11-(2-hydroxyethylthio)undecanoate
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In acetonitrile at 20℃; Visible light; | 95% |
Conditions | Yield |
---|---|
Stage #1: methanol; Methyl 10-undecenoate With ozone In methanol at 0℃; Stage #2: With semicarbazide hydrochloride at 0 - 20℃; Reagent/catalyst; Inert atmosphere; | 95% |
Methyl 10-undecenoate
1,4-diacetoxybut-2-ene
Conditions | Yield |
---|---|
Stage #1: Methyl 10-undecenoate; 1,4-diacetoxybut-2-ene With [1,3-bis(2,6-di-isopropylphenyl)-2-imidazolidinylidene]dichloro(o-isopropoxyphenylmethylene)ruthenium(II) In dichloromethane at 45℃; for 6h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With methanol; potassium hydroxide In dichloromethane at 20℃; | 94% |
The 10-Undecenoic acid,methyl ester is an organic compound with the formula C12H22O2. The IUPAC name of this chemical is methyl undec-10-enoate. With the CAS registry number 111-81-9, it is also named as Methyl 10-undecenate. The product's category is Aromatic Esters. Besides, it should be stored in a cool and well-ventilated place.
Physical properties about 10-Undecenoic acid,methyl ester are: (1)ACD/LogP: 4.45; (2)ACD/LogD (pH 5.5): 4.45; (3)ACD/LogD (pH 7.4): 4.45; (4)ACD/BCF (pH 5.5): 1416.9; (5)ACD/BCF (pH 7.4): 1416.9; (6)ACD/KOC (pH 5.5): 6270.86; (7)ACD/KOC (pH 7.4): 6270.86; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 10; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.438; (12)Molar Refractivity: 59.14 cm3; (13)Molar Volume: 225.1 cm3; (14)Polarizability: 23.44×10-24cm3; (15)Surface Tension: 29.1 dyne/cm; (16)Density: 0.88 g/cm3; (17)Flash Point: 99.3 °C; (18)Enthalpy of Vaporization: 48.45 kJ/mol; (19)Boiling Point: 247.3 °C at 760 mmHg; (20)Vapour Pressure: 0.0259 mmHg at 25°C.
Preparation of 10-Undecenoic acid,methyl ester: this chemical can be prepared by methanol and undec-10-enoic acid. This reaction is a kind of Esterification. This reaction will need reagent H2SO4. The reaction time is 3 hours by heating.
Uses of 10-Undecenoic acid,methyl ester: it can be used to produce 10-oxo-decanoic acid methyl ester. It will need reagent ozone.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)CCCCCCCC\C=C
(2)InChI: InChI=1/C12H22O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h3H,1,4-11H2,2H3
(3)InChIKey: KISVAASFGZJBCY-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C12H22O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h3H,1,4-11H2,2H3
(5)Std. InChIKey: KISVAASFGZJBCY-UHFFFAOYSA-N
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