Conditions | Yield |
---|---|
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Stage #2: cyclohexanone In tetrahydrofuran at 0 - 20℃; | 99.3% |
With potassium hydroxide In dimethyl sulfoxide at 15 - 17℃; for 2h; | 98% |
Stage #1: acetylene With ammonia; sodium at -78℃; Stage #2: cyclohexanone In diethyl ether at -78℃; for 12h; | 97% |
Conditions | Yield |
---|---|
With methanol; oxo[hexa(trifluoroacetato)]tetrazinc for 48h; Reflux; Inert atmosphere; | 96% |
[t-Bu2SnOH(Cl)]2 In methanol for 24h; Heating; | 86 % Chromat. |
1-((trimethylsilyl)ethynyl)cyclohexanol
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 12h; Inert atmosphere; | 95% |
With tetrabutyl ammonium fluoride In tetrahydrofuran | |
With methanol; potassium carbonate at 20℃; for 12h; Inert atmosphere; | |
With potassium carbonate In tetrahydrofuran; methanol | |
With potassium carbonate In methanol under 760.051 Torr; for 1h; |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; water In dimethyl sulfoxide at 20℃; for 2h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; | 94% |
With caesium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; Inert atmosphere; Green chemistry; | 61% |
With caesium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; Sonogashira Cross-Coupling; | |
With water; caesium carbonate In dimethyl sulfoxide at 60℃; for 8h; Inert atmosphere; |
1-(((1-ethynylcyclohexyl)oxy)methyl)-4-methoxybenzene
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 3h; Irradiation; Green chemistry; | 88% |
With sodium hydrogen sulfate; eosin; dihydrogen peroxide In water; acetonitrile for 25h; Irradiation; | 56% |
2-(1-ethynyl-cyclohexyloxy)-tetrahydro-pyran
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In methanol; N,N-dimethyl-formamide at 110℃; for 19h; | 84% |
With iron(III) p-toluenesulfonate hexahydrate In methanol at 20℃; for 2h; | 77% |
triethyl((1-ethynylcyclohexyl)oxy)silane
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With potassium fluoride; Tetraethylene glycol at 20℃; for 24h; | 82% |
trimethylaluminum
sodium acetylide
cyclohexanone
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene; xylene for 3h; Ambient temperature; | 81% |
O-(p-nitrobenzoyl)-1-ethynylcyclohexanol
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With sodium azide In methanol at 40℃; for 6h; | 79% |
Conditions | Yield |
---|---|
Stage #1: acetylenemagnesium bromide In tetrahydrofuran; tetradecyl(trihexyl)phosphonium decanoate at -78 - 20℃; Stage #2: cyclohexanone In tetradecyl(trihexyl)phosphonium decanoate; toluene for 16h; Stage #3: With water In tetradecyl(trihexyl)phosphonium decanoate; toluene | 78% |
In tetrahydrofuran at -10 - 20℃; for 2.16667h; | 70% |
In tetrahydrofuran Heating; | 61% |
cyclohexanone
acetylene
A
1-ethynyl-1-(vinyloxy)cyclohexane
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With potassium hydroxide semihydrate In dimethyl sulfoxide at 90℃; under 15201 - 19001.3 Torr; for 1h; | A 40% B n/a |
With potassium hydroxide semihydrate In dimethyl sulfoxide at 80℃; for 0.5h; High pressure; | A 11% B 40% |
With potassium hydroxide semihydrate In dimethyl sulfoxide at 90℃; for 1h; High pressure; | A 40% B 12% |
tetrachloromethane
sodium acetylide
cyclohexanone
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
at 130℃; |
diethyl ether
sodium acetylide
cyclohexanone
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With diethyl ether | |
With ammonia | |
With ammonia |
tetrachloromethane
cyclohexanone
acetylene
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
at 85℃; under 14710.2 Torr; |
cyclohexanone
acetylene
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With sodium hydroxide at 85℃; under 14710.2 Torr; | |
With potassium hydroxide at 85℃; under 14710.2 Torr; |
Conditions | Yield |
---|---|
With diethyl ether; sodium amide nachfolgend Einleiten von Acetylen unter Druck; |
cyclohexanone
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With potassium hydroxide; diethyl ether Einleiten von Acetylen; | |
With diethyl ether; sodium amide nachfolgend Einleiten von Acetylen unter Druck; |
Conditions | Yield |
---|---|
With diethyl ether | |
With diethyl ether |
1-ethynyl-1-(trimethylsiloxy)cyclohexane
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
With sodium hydroxide; n-butyllithium 1.) THF, -78 deg C; 2.) MeOH; Yield given. Multistep reaction; | |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: cyclohexanone at -78 - 20℃; Stage #3: With potassium carbonate In methanol |
cyclohexanone
acetylene
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
at 85℃; under 14710.2 Torr; |
diethyl ether
cyclohexanone
acetylene
A
1,2-di(1-hydroxycyclohexyl)acetylene
B
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
unter Kuehlung; |
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium 2-methylbutan-2-olate |
3-(1-hydroxycyclohexyl)propiolic acid
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
at 200℃; under 20 Torr; |
1,2-di(1-hydroxycyclohexyl)acetylene
A
cyclohexanone
B
1-Ethynyl-1-cyclohexanol
C
acetylene
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; |
cyclohexanone
1-Ethynyl-1-cyclohexanol
1,2-di(1-hydroxycyclohexyl)acetylene
Conditions | Yield |
---|---|
Stage #1: 1-Ethynylcyclohexan-1-ol With ethylmagnesium bromide In tetrahydrofuran at 23 - 80℃; Stage #2: cyclohexanone In tetrahydrofuran at 23 - 25℃; Stage #3: With ammonium chloride In tetrahydrofuran; water | 100% |
With sodium hydroxide; tetrabutylammomium bromide In toluene at 70℃; for 2h; | 89% |
Stage #1: 1-Ethynylcyclohexan-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: cyclohexanone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -78 - 20℃; for 14h; | 74% |
acetic anhydride
1-Ethynyl-1-cyclohexanol
1-acetoxy-1-ethynyl cyclohexane
Conditions | Yield |
---|---|
indium(III) chloride In acetonitrile at 20℃; for 0.5h; | 100% |
With magnesium(II) perchlorate at 20℃; for 0.5h; | 100% |
tetrafluoroboric acid; silica gel at 20℃; for 6h; | 96% |
Conditions | Yield |
---|---|
With NH4NO3-exchanged zeolite HSZ-320 In chlorobenzene at 130℃; for 4h; | 100% |
With aliquat 366; water; PtCl4-CO In various solvent(s) at 110℃; under 1034.3 Torr; for 4.5h; | 97% |
With Dowex-50; acetic acid Rupe rearrangement; Heating; | 95% |
phenyl isocyanate
1-Ethynyl-1-cyclohexanol
1-ethynylcyclohexyl phenylcarbamate
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h; | 100% |
In 1,2-dichloro-ethane at 20℃; for 16h; | 82% |
With 1-methyl-pyrrolidin-2-one |
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20 - 40℃; Addition; | 100% |
Conditions | Yield |
---|---|
With trifluoroacetic acid at 30 - 35℃; for 12h; Addition; | 100% |
1-Ethynyl-1-cyclohexanol
bis adduct of diethylene glycol divinyl ether and diethylene glycol
Conditions | Yield |
---|---|
With trifluoroacetic acid at 30 - 35℃; for 10h; Addition; | 100% |
1-Ethynyl-1-cyclohexanol
Conditions | Yield |
---|---|
Stage #1: 1-Ethynylcyclohexan-1-ol With sodium hydride In N,N-dimethyl-formamide Stage #2: (E)-4-Ethoxy-5,5,6,6,6-pentafluoro-1-phenyl-3-(phenylsulfonyl)hex-3-en-1-yne In N,N-dimethyl-formamide at 0℃; for 0.166667h; Further stages.; | 100% |
1-Ethynyl-1-cyclohexanol
1-methyl-3-iodo-1H-indole-2-carbaldehyde
3-(1-hydroxycyclohexylethynyl)-1-methylindole-2-carboxaldehyde
Conditions | Yield |
---|---|
With triethylamine; 2percent PdCl2(PPh3)2 at 60℃; for 18h; Sonogashira coupling; | 100% |
Conditions | Yield |
---|---|
With copper(l) iodide In methanol; N,N-dimethyl-formamide at 100℃; Inert atmosphere; | 100% |
1-Ethynyl-1-cyclohexanol
benzyl azide
(1-benzyl-1H-[1,2,3]triazol-4-yl)-cyclohexylmethanol
Conditions | Yield |
---|---|
With bis[1-(4-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-3-ylidine]copper(I) hexafluorophosphate In neat (no solvent) at 20℃; for 0.0833333h; | 99% |
With (2,4-dimesityl-4,5-dihydro-1H-naphtho[1,8-ef][1,3]diazocin-3(2H)-ylidene)copper(I) bromide at 25℃; Inert atmosphere; Schlenk technique; | 99% |
With copper-supported ionic liquid catalyst In ethanol; water at 20℃; for 1.5h; Huisgen cycloaddition; | 98% |
Conditions | Yield |
---|---|
With copper(l) iodide; ethyl bromoacetate; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; | 99% |
With N,N,N,N,-tetramethylethylenediamine; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride In acetonitrile at 24℃; for 24h; | 99% |
With 1-n-butyl-3-methylimidazolim bromide; copper(II) trifluoroacetate hydrate name... In water at 50℃; for 24h; Solvent; Green chemistry; | 99% |
Phenylselenyl chloride
1-Ethynyl-1-cyclohexanol
1-(E-2'-phenylseleno-1'-chloroethenyl)cyclohexanol
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling; | 99% |
With piperidine; copper(l) iodide; bis(acetato)bis(triphenylphosphine)palladium(0) In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 20℃; Inert atmosphere; | 97% |
carbon dioxide
1-Ethynyl-1-cyclohexanol
4-methylidene-1,3-dioxaspiro[4.5]decan-2-one
Conditions | Yield |
---|---|
With potassium acetate; silver(I) iodide In N,N-dimethyl-formamide at 45℃; under 750.075 Torr; for 24h; | 99% |
With (dimethylamino)methyl-polystyrene supported copper(I) iodide at 40℃; under 105011 Torr; for 24h; Autoclave; | 96% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 30℃; under 7500.75 Torr; for 12h; Catalytic behavior; Autoclave; Green chemistry; | 96% |
para-iodoanisole
1-Ethynyl-1-cyclohexanol
1-[2-(4-methoxyphenyl)ethynyl]cyclohexanol
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride at 55℃; for 3h; Sonogashira Cross-Coupling; Ionic liquid; Green chemistry; | 99% |
With piperidine; copper(l) iodide; bis(triphenylphosphine) palladium (Il) acetate In N,N-dimethyl-formamide at 60℃; for 2h; | 98% |
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling; | 91% |
Conditions | Yield |
---|---|
With sodium iodide In tetrahydrofuran at 20℃; for 1h; stereoselective reaction; | 99% |
With platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane; tri-tert-butyl phosphine In tetrahydrofuran at 20℃; Inert atmosphere; stereoselective reaction; | 93% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; triphenylphosphine In acetone at 50℃; for 16h; | 92% |
Isopropenyl acetate
1-Ethynyl-1-cyclohexanol
1-acetoxy-1-ethynyl cyclohexane
Conditions | Yield |
---|---|
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene at 25℃; for 15h; | 99% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride at 55℃; for 3h; Sonogashira Cross-Coupling; Ionic liquid; Green chemistry; | 99% |
With piperidine In water; acetonitrile at 40℃; for 4h; Sonogashira coupling; | 95% |
With sodium hydroxide; palladium diacetate In water; acetone at 60℃; for 1h; Sonogashira reaction; | 94% |
With [bbim]BF4; triethylamine; palladium dichloride at 30℃; for 2.5h; Sonogashira reaction; sonication; | 72% |
Conditions | Yield |
---|---|
With triethylamine; copper carbide In 1,4-dioxane at 60℃; for 2h; | 99% |
1-Fluoro-2-iodobenzene
1-Ethynyl-1-cyclohexanol
1-(2-fluorophenylethynyl)cyclohexanol
Conditions | Yield |
---|---|
With copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride at 80℃; Sonogashira coupling; | 99% |
1-Ethynyl-1-cyclohexanol
carbonic acid dimethyl ester
methyl 1,1-pentamethyleneprop-2-ynyl carbonate
Conditions | Yield |
---|---|
Stage #1: carbonic acid dimethyl ester With lanthanum (III) nitrate * water; TOP at 20℃; Stage #2: 1-Ethynylcyclohexan-1-ol for 10h; Molecular sieve; Reflux; | 99% |
Stage #1: carbonic acid dimethyl ester With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 20℃; Stage #2: 1-Ethynylcyclohexan-1-ol for 12h; Reflux; chemoselective reaction; | 97% |
With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 110℃; for 12h; Reagent/catalyst; Molecular sieve; | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique; | 99% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 0 - 20℃; for 6.5h; | 98% |
Conditions | Yield |
---|---|
With (η5-C5Me5)Ru(P(i-Pr)3)Cl In dichloromethane at 20℃; for 0.0166667h; | 99% |
phenethyl azide
1-Ethynyl-1-cyclohexanol
1-(1-phenethyl-1H-1,2,3-triazol-4-yl)cyclohexanol
Conditions | Yield |
---|---|
With bis[1-(4-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-3-ylidine]copper(I) hexafluorophosphate In neat (no solvent) at 20℃; for 1.3h; | 99% |
With copper(ll) sulfate pentahydrate; betaine; sodium L-ascorbate In water at 30℃; for 24h; | 96% |
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; β‐cyclodextrin In water at 20℃; for 0.2h; | 95% |
1-Ethynyl-1-cyclohexanol
benzyl azide
1-(1-phenethyl-1H-1,2,3-triazol-4-yl)cyclohexanol
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol | 99% |
1-Ethynyl-1-cyclohexanol
1-[(Z)-2-iodoethenyl]cyclohexanol
Conditions | Yield |
---|---|
Stage #1: 1-Ethynylcyclohexan-1-ol With triethyl borane; dichloroindium hydride In tetrahydrofuran; hexane at -78℃; for 2.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
Reported in EPA TSCA Inventory.
The 1-Ethynyl-1-cyclohexanol with CAS registry number of 78-27-3 is also known as 1-Ethynyl-1-cyclohexanol. The IUPAC name and product name are tha same. It belongs to product categories of Biphenyl & Diphenyl ether; Acetylenes; Acetylenic Alcohols & Their Derivatives; Alkynes; Organic Building Blocks; Terminal. Its EINECS registry number is 201-100-9. In addition, the formula is C8H12O and the molecular weight is 124.18. This chemical is a colorless liquid that soluble in water. It may cause inflammation to the skin or other mucous membranes and may cause damage to health. This chemical should be sealed in cool place without light.
Physical properties about 1-Ethynyl-1-cyclohexanol are: (1)ACD/LogP: 1.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.73; (4)ACD/LogD (pH 7.4): 1.73; (5)ACD/BCF (pH 5.5): 12.14; (6)ACD/BCF (pH 7.4): 12.14; (7)ACD/KOC (pH 5.5): 207.77; (8)ACD/KOC (pH 7.4): 207.77; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.493; (13)Molar Refractivity: 36.38 cm3; (14)Molar Volume: 125 cm3; (15)Surface Tension: 39.5 dyne/cm; (16)Density: 0.99 g/cm3; (17)Flash Point: 62.8 °C; (18)Enthalpy of Vaporization: 47.77 kJ/mol; (19)Boiling Point: 174 °C at 760 mmHg; (20)Vapour Pressure: 0.384 mmHg at 25 °C.
Preparation of 1-Ethynyl-1-cyclohexanol. Firstly, passing dry acetylene into liquid ammonia, then adding sodium and dropping cyclohexanone to solution. The reaction is continued for 20 hours until ammonia is evaporated completely. Secondly, adding ice water for residue decomposition and 50% sulfuric acid for acidification. After extraction of the water layer with ether, mixing organic layer and ether extract. At last, collecting distillate at pressure of 18.67kPa to obtain the product when ether has been steamed. The yield is about 65-74%.
Uses of 1-Ethynyl-1-cyclohexanol: it is used to produce 2-(1-ethynyl-cyclohexyloxy)-tetrahydro-pyran by reaction with 3,4-dihydro-2H-pyran. The reaction occurs with catalyst triphenylphosphine hydrobromide and solvent CH2Cl2 with other condition of ambient temperature for 23 hours. The yield is about 93%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Furthermore, this chemical is harmful by inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C#CC1(CCCCC1)O
2. InChI: InChI=1S/C8H12O/c1-2-8(9)6-4-3-5-7-8/h1,9H,3-7H2
3. InChIKey: QYLFHLNFIHBCPR-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 161, 1955. | |
rabbit | LD50 | skin | 1mL/kg (1mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. | |
rat | LD50 | oral | 600uL/kg (0.6mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. |
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