Conditions | Yield |
---|---|
With potassium salt of 1,3-diaminopropane In tetrahydrofuran at 0℃; for 0.5h; other reagent; | 97% |
With sodium amide; mineral oil at 210℃; |
(Z)-1-dimethylphenylsilyl-2-iodo-1-dodecene
1-dodecyne
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dimethyl sulfoxide at 80℃; for 0.25h; | 95% |
1-trimethylsilyldodec-1-yne
1-dodecyne
Conditions | Yield |
---|---|
With silver nitrate In water; acetone at 20 - 55℃; for 48h; | 92% |
5-dodecyne
1-dodecyne
Conditions | Yield |
---|---|
With lithium 2-aminoethylamide In ethylenediamine for 0.333333h; amide-hydrocarbon ratio 3.5:1; | 85% |
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 4℃; for 36h; Horner-Wadsworth-Emmons reaction; | 70% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; benzene at 50 - 65℃; for 4h; | 52.3% |
lithium 1-phenylethenolate
1-dodecenyl phenyl selenone
A
1-dodecyne
B
2-decylcyclopropyl phenyl ketone
Conditions | Yield |
---|---|
A 19% B 41% |
1,2-Dibromododecane
1-dodecyne
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide; sodium hydride 1.) water, EtOH, reflux, 2 h, 2.) DMSO, 10 deg C, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With ammonia; sodium amide under 5884.06 Torr; | |
With ammonia; N,N-dimethyl-formamide nach Entfernung des Ammoniaks bei 65-70grad; |
Conditions | Yield |
---|---|
With ammonia unter Druck; |
Conditions | Yield |
---|---|
With sodium at 180 - 220℃; |
Conditions | Yield |
---|---|
(i) , (ii) NaNH2, liq. NH3; Multistep reaction; |
methanol
cyclododecene
A
1-dodecene
B
1-dodecyne
C
Cyclododecyl methyl ether
D
bicyclo<7.3.0>dodecane
Conditions | Yield |
---|---|
for 60h; Irradiation; | A 2 % Chromat. B 4 % Chromat. C 11 % Chromat. D 15 % Chromat. |
cyclododecene
A
1-dodecene
B
1-dodecyne
C
cyclododecane
D
Cyclododecyl methyl ether
E
bicyclo<7.3.0>dodecane
F
1,2-epoxycyclododecane
Conditions | Yield |
---|---|
Product distribution; Mechanism; Irradiation; yields in pentane or methanol or methanol-d1; |
cyclododecene
A
1-dodecene
B
1-dodecyne
C
Cyclododecyl methyl ether
D
bicyclo<7.3.0>dodecane
Conditions | Yield |
---|---|
In methanol for 60h; Irradiation; | A 2 % Chromat. B 4 % Chromat. C 11 % Chromat. D 15 % Chromat. |
Conditions | Yield |
---|---|
In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 90℃; for 2h; |
Conditions | Yield |
---|---|
With hydrogenchloride; Schwartz's reagent; 2,2,6,6-tetramethylpiperidinyl-lithium Yield given; Multistep reaction; |
Conditions | Yield |
---|---|
at 210℃; |
Conditions | Yield |
---|---|
at 220℃; |
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20 - 68℃; | |
With sodium hydride In dimethyl sulfoxide; mineral oil at 20 - 68℃; Reagent/catalyst; Solvent; |
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With indium(III) chloride; triethyl borane; diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 2.5h; Stage #2: With hydrogen cation In tetrahydrofuran Further stages.; | 100% |
Stage #1: 1-dodecyne With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane | 98% |
With pyridine; Dimethylphenylsilane; water In acetonitrile at 80℃; for 8h; | 98% |
1-dodecyne
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine; N,N-dimethyl-formamide at 20℃; for 36h; Heck reaction; | 100% |
2-bromo-6-(3-hydroxy-3-methyl-1-butynyl)-4-octyloxypyridine
1-dodecyne
2-(1-dodecynyl)-6-(3-hydroxy-3-methyl-1-butynyl)-4-octoxypyridine
Conditions | Yield |
---|---|
With copper(l) iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 2.5h; Sonogashira reaction; | 100% |
1-dodecyne
(E)-1-triphenylgermyl-1-dodecene
Conditions | Yield |
---|---|
With butan-1-ol In tetrahydrofuran 1-dodecyne (0.5 mmol) treated with germylmanganate (0.6 mmol) in THF inthe presence of n-BuOH (2.0 mmol) at 25°C for 4.5 h; | 100% |
Conditions | Yield |
---|---|
With copper(II) sulphate hydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; for 48h; Huisgen cycloaddition; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With n-butyllithium In tetrahydrofuran at 5℃; for 0.5h; Inert atmosphere; Stage #2: paracetaldehyde In tetrahydrofuran at 5 - 20℃; | 100% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; Cooling with acetone-dry ice; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran Ambient temperature; | 99% |
With triethylamine In water for 2h; Sonogashira Cross-Coupling; Heating; | 78% |
1-dodecyne
tetracosa-11,13-diyne
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; ethyl bromoacetate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; | 99% |
With 1,10-Phenanthroline; dicobalt octacarbonyl; carbon monoxide In acetonitrile at 80℃; under 760 Torr; for 18h; | 91% |
With N,N,N,N,-tetramethylethylenediamine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; copper(l) chloride at 20℃; for 7h; Glaser oxidative coupling; | 90% |
1-dodecyne
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 24h; Heck reaction; | 99% |
Conditions | Yield |
---|---|
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; | 99% |
With diethyl ether for 24h; Milling; | 86% |
With palladium 10% on activated carbon; hydrogen at 20℃; for 24h; Neat (no solvent); | 83% |
1-dodecyne
1-deuterio-1-dodecyne
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With potassium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With water-d2 In acetonitrile at 20℃; for 1h; Inert atmosphere; | 99% |
With n-butyllithium; water-d2 In diethyl ether; hexane | 69% |
With water-d2 at 50℃; for 8h; | 65% |
With water-d2 at 70℃; | |
With water-d2; potassium carbonate In acetonitrile at 50℃; for 24.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
triethyl borane In hexane; benzene addn. of Et3B in hexane to a soln. of acetylene-compd. and a slight excess of Ph3GeH in benzene, heating at 60°C for 2 h; evapn., purifn. by column chromy. or preparative thin-layer chromy. on silica gel,; elem. anal.; isomer ratio Z/E=<1/20 (detd. by GC, NMR); | 99% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 100℃; for 36h; Sonogashira coupling; Inert atmosphere; | 99% |
1-dodecyne
2-bromo-4-nitrotoluene
2-(dodec-1-yn-1-yl)-1-methyl-4-nitrobenzene
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); triethylamine; XPhos In water at 20℃; Sonogashira coupling; Inert atmosphere; Micellar solution; | 99% |
With dichloro bis(acetonitrile) palladium(II); SPGS-550-M; NOK; triethylamine; XPhos In water for 24h; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere; Sealed tube; | 98% |
1-dodecyne
4β-azido-4-deoxy-4′-demethylepipodophyllotoxin
4'-O-demethyl-4β-[(4-decyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; L-ascorbic acid sodium salt In water; tert-butyl alcohol at 20℃; for 8h; | 99% |
1-dodecyne
1-(2,6-dibromo-phenyl)-1H-pyrrole
1-(2,6-di(dodec-1-yn-1-yl)phenyl)-1H-pyrrole
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tri-tert-butyl phosphine; diisopropylamine In 1,4-dioxane; toluene at 20℃; Inert atmosphere; | 99% |
1-dodecyne
1,1'-sulfinylbisbenzene
A
racemic methyl phenyl sulfoxide
B
1-(dodec-1-yn-1-yl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne; 1,1'-sulfinylbisbenzene With dichloro-[1,3-bis(2,6-diisopropylpenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II); lithium tert-butoxide In tetrahydrofuran at 70℃; for 6h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 98% B 99% |
1-dodecyne
1-iodo-dodeca-1-yne
Conditions | Yield |
---|---|
With N-iodo-succinimide; silver nitrate In acetone at 20℃; for 1h; Darkness; | 98% |
With N-iodo-succinimide; silver nitrate In acetone at 20℃; for 1h; Darkness; | 98% |
With N-iodo-succinimide; acetic acid In acetonitrile at 80℃; for 1.5h; Molecular sieve; | 93% |
1-dodecyne
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20℃; for 24h; Heck reaction; | 98% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; for 3.5h; Substitution; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: methyl chloroformate In tetrahydrofuran at 20℃; | 98% |
Conditions | Yield |
---|---|
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; palladium diacetate; triethylamine In water at 20℃; Sonogashira coupling; Inert atmosphere; Micellar solution; | 98% |
1-dodecyne
(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran
C47H56O5
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 20℃; for 1h; Sonogashira coupling; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 4-trifluoromethylbenzoic acid; bis[2-(diphenylphosphino)phenyl] ether In ethanol; 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere; Sealed tube; regioselective reaction; | 98% |
1-dodecyne
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With benzo[1,3,2]dioxaborole In tetrahydrofuran at 70℃; for 2h; Stage #2: tert-butyl (2R,4S)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water at 85℃; for 5h; Suzuki-Miyaura Coupling; | 98% |
1-dodecyne
Conditions | Yield |
---|---|
Stage #1: 1-dodecyne With benzo[1,3,2]dioxaborole In tetrahydrofuran at 70℃; for 2h; Stage #2: tert-butyl (2S,4R)-4-((4-bromobenzyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water at 85℃; for 5h; Suzuki-Miyaura Coupling; | 98% |
1-dodecyne
(Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid
Conditions | Yield |
---|---|
With copper diacetate In methanol at 50℃; Temperature; Flow reactor; Sonication; | 98% |
With copper diacetate In methanol |
1-dodecyne
1-iodo-2-((2-methylallyl)oxy)benzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; Green chemistry; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; | 98% |
1-dodecyne
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.25h; Microwave irradiation; Inert atmosphere; Sealed tube; Green chemistry; | 98% |
The 1-Dodecyne, with the CAS registry number 765-03-7 and EINECS registry number 212-134-9, has the systematic name and IUPAC name of dodec-1-yne. It is a kind of clear colorless to light yellow liquid, and belongs to the following procuct categories: Acetylenes; Acetylenic Hydrocarbons; Alkynes; Organic Building Blocks; Termina. And the molecular formula of the chemical is C12H22.
The characteristics of 1-Dodecyne are as followings: (1)ACD/LogP: 5.78; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.78; (4)ACD/LogD (pH 7.4): 5.78; (5)ACD/BCF (pH 5.5): 14545.38; (6)ACD/BCF (pH 7.4): 14545.38; (7)ACD/KOC (pH 5.5): 33209.78; (8)ACD/KOC (pH 7.4): 33209.78; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.44; (14)Molar Refractivity: 55.47 cm3; (15)Molar Volume: 210.3 cm3; (16)Polarizability: 21.99×10-24cm3; (17)Surface Tension: 29 dyne/cm; (18)Density: 0.79 g/cm3; (19)Flash Point: 79.4 °C; (20)Enthalpy of Vaporization: 43.29 kJ/mol; (21)Boiling Point: 215 °C at 760 mmHg; (22)Vapour Pressure: 0.222 mmHg at 25°C.
Uses of 1-Dodecyne: It can react with butane-1-thiol to produce 1-butylsulfanyl-dodec-1-ene. This reaction will need reagent Et3B and MeOH, and the menstruum hexan and benzene. The reaction time is 4 hours with temperature of 25°C, and the yield is about 60%.
You should be cautious while dealing with this chemical. It has risk of serious damage to eyes. Therefore, you had better take the following instructions: Wear suitable eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: C#CCCCCCCCCCC
(2)InChI: InChI=1/C12H22/c1-3-5-7-9-11-12-10-8-6-4-2/h1H,4-12H2,2H3
(3)InChIKey: ZVDBUOGYYYNMQI-UHFFFAOYAI
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