Welcome to LookChem.com Sign In|Join Free

CAS

  • or

502-49-8

Post Buying Request

502-49-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

502-49-8 Usage

Uses

Different sources of media describe the Uses of 502-49-8 differently. You can refer to the following data:
1. Cyclooctanone is a aliphatic cycle that exhibited inhibitory activity towards aldosterone synthase, a promising therapeutic target for the treatment of cardiovascular diseases related to abnormally high aldosterone level.
2. Cyclooctanone is a aliphatic cycle that exhibited inhibitory activity towards aldosterone synthase, a promising therapeutic target for the treatment of cardiovascular diseases related to abnormally high aldosterone level. It is also used in the synthesis of 14-membered lactones.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 5276, 1970 DOI: 10.1021/ja00720a078The Journal of Organic Chemistry, 49, p. 3912, 1984 DOI: 10.1021/jo00195a007Tetrahedron Letters, 36, p. 2921, 1995 DOI: 10.1016/0040-4039(95)00467-Q

Purification Methods

Purify the ketone by sublimation after drying with Linde type 13X molecular sieves. The semicarbazone has m 168-169o (from dioxane) [Kohler et al. J Am Chem Soc 61 1060 1939]. The oxime has m 36-37o after subliming at high vacuum or distillation and has b 128-129o /14mm. The iso-oxime has m 72-73o [Ruzicka et al. Helv Chim Acta 32 548 1949]. [Beilstein 7 III 77, 7 IV 49.]

Check Digit Verification of cas no

The CAS Registry Mumber 502-49-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 2 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 502-49:
(5*5)+(4*0)+(3*2)+(2*4)+(1*9)=48
48 % 10 = 8
So 502-49-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-7H2

502-49-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (B20911)  Cyclooctanone, 98%   

  • 502-49-8

  • 25g

  • 282.0CNY

  • Detail
  • Alfa Aesar

  • (B20911)  Cyclooctanone, 98%   

  • 502-49-8

  • 100g

  • 845.0CNY

  • Detail
  • Alfa Aesar

  • (B20911)  Cyclooctanone, 98%   

  • 502-49-8

  • 500g

  • 3380.0CNY

  • Detail

502-49-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclooctanone

1.2 Other means of identification

Product number -
Other names CYCLOOCTANONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:502-49-8 SDS

502-49-8Synthetic route

cyclooctanol
696-71-9

cyclooctanol

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate In tert-butyl alcohol at 90℃; for 0.5h;100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.5h;100%
With ruthenium trichloride; iodobenzene; potassium peroxymonosulfate In water; acetonitrile at 20℃; for 0.5h; Inert atmosphere;100%
Cyclooctan
292-64-8

Cyclooctan

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h;98%
With oxygen; isobutyraldehyde; vanadium-substituted V-MCM-41 (A) zeolite In acetone at 25℃; for 24h;83%
With potassium permanganate; borontrifluoride acetic acid In acetonitrile at 23℃; for 0.166667h;55%
Cyclooctene oxide
286-62-4

Cyclooctene oxide

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With lithium iodide In xylene at 140℃; for 6h;98%
With lithium iodide In xylene at 140℃; for 6h; Product distribution; other temperatures, other times; various concentrations of catalyst; other catalyst; without a solvent;
cyclooctylamine
5452-37-9

cyclooctylamine

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With zinc dichromate trihydrate at 20℃; grinding; neat (no solvent); chemoselective reaction;98%
With 3-carboxypyridinium dichromate In acetonitrile at 20℃; for 0.25h;97%
With potassium permanganate; copper(II) sulfate In dichloromethane for 24h; Heating;90%
cyclooctyl methyl ether
13213-32-6

cyclooctyl methyl ether

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
Stage #1: cyclooctyl methyl ether With bromine In dichloromethane; water for 1h; Reflux;
Stage #2: With dihydrogen peroxide In dichloromethane; water for 4h; Reflux;
97%

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water at 150℃; for 12h; Sealed tube;A 4%
B 96%
ethyl 2-oxocyclooctane-1-carboxylate
4017-56-5

ethyl 2-oxocyclooctane-1-carboxylate

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With sodio-propane-1,2-diol in anhydrous propane-1,2-diol at 80 - 85℃; for 0.5h;95%
cyclooctanone semicarbazone
40338-24-7

cyclooctanone semicarbazone

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogenchloride; Tonsil In ethyl acetate for 2h; Heating;94.1%
carbon monoxide
201230-82-2

carbon monoxide

cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

A

cycloactanone
502-49-8

cycloactanone

trans-9-oxa-bicyclo[6.2.0]decan-10-one

trans-9-oxa-bicyclo[6.2.0]decan-10-one

Conditions
ConditionsYield
With [(salph)Cr(THF)2][Co(CO)4] In 1,2-dimethoxyethane at 60℃; under 5171.48 Torr; for 24h;A 3%
B 94%
1,1-dimethoxycyclooctane
25632-03-5

1,1-dimethoxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;93%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
1,4-dioxaspiro<4.7>dodecane
183-03-9

1,4-dioxaspiro<4.7>dodecane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;92%
With Montmorillonite K 10; water In acetone for 0.5h; Heating;87%
indium(III) chloride In methanol; water for 1.5h; Heating;85%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
3,3-dimethyl-1,5-dioxaspiro<5.7>tridecane
27889-58-3

3,3-dimethyl-1,5-dioxaspiro<5.7>tridecane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h;91%
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;
2-bromocyclooctan-1-one
39261-18-2

2-bromocyclooctan-1-one

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With diphosphorus tetraiodide In dichloromethane at 25℃; for 7h;91%
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 70℃; for 24h; Temperature; Wacker Oxidation;90%
With dihydrogen peroxide; tetraphenylphosphonium; sodium hydrogencarbonate; WO(O2)(QO)4 In acetonitrile at 25℃; for 0.5h;74%
Stage #1: cis-Cyclooctene With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #2: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In tetrahydrofuran; dichloromethane at 20℃; Molecular sieve;
53%
1,1-bis(phenylthio)cyclooctane
85895-35-8

1,1-bis(phenylthio)cyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;87%
cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In toluene at 0℃; for 2h;87%
t-BuOSmI2 In tetrahydrofuran at 60℃; for 4h;83%
cyclooctanol
696-71-9

cyclooctanol

Dess-Martin periodane
87413-09-0

Dess-Martin periodane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
In dichloromethane at 25℃; for 2.1h; Product distribution; Mechanism; var. primary and secondary alcohols, var. 12-I-5 species; other solvents and relation time, var. concentrations of oxidant, in the presence of different labile groups in the molecule;86%
(cyclooctyloxy)trimethylsilane
40756-11-4

(cyclooctyloxy)trimethylsilane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With sodium bromate; ammonium chloride In water; acetonitrile at 80℃; for 0.833333h;82%
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

A

cycloactanone
502-49-8

cycloactanone

B

cis-1,2-epoxycyclooctane
4925-71-7

cis-1,2-epoxycyclooctane

Conditions
ConditionsYield
With oxygen; magnesium oxide supported polytitazane-tin tetrachloride In 1,4-dioxane at 80℃; for 20h;A n/a
B 81%
Cyclooctan
292-64-8

Cyclooctan

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With CoO40W12(5-)*3C30H24CoN6*9.5H2O*2H(1+); dihydrogen peroxide In acetonitrile at 80℃; for 9h; Inert atmosphere;A 80%
B 19%
With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Catalytic behavior; Overall yield = 89 %Spectr.;A 77%
B 13%
With oxygen; copper diacetate; acetaldehyde In dichloromethane; acetonitrile at 70℃; under 760.051 Torr; for 24h; Catalytic behavior; Inert atmosphere;A 74%
B 8%
1,2-dicyclooctylidenehydrazine
53867-57-5

1,2-dicyclooctylidenehydrazine

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With HOF* CH3CN In dichloromethane at 0℃; for 0.0166667h;80%
{[Cp*Ru(CO)2]2(μ-H)}+OTf-

{[Cp*Ru(CO)2]2(μ-H)}+OTf-

cyclooctanol
696-71-9

cyclooctanol

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With hydrogen In 1,2-dichloro-benzene80%
Cyclooctan
292-64-8

Cyclooctan

A

cycloactanone
502-49-8

cycloactanone

B

cyclooctylhydroperoxide
5130-47-2

cyclooctylhydroperoxide

Conditions
ConditionsYield
With HO40PVW11(14-)*4C16H36N(1+); dihydrogen peroxide In acetonitrile at 80℃; for 12h; Inert atmosphere;A 23%
B 77%
With 5,10,15,20-tetrakis(4-chlorophenyl)porphyrinatocopper(II); T(o-Cl)PPCo; oxygen at 110℃; under 10501.1 Torr; for 8h;
cyclooctanone thioketal
183-04-0

cyclooctanone thioketal

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With formaldehyd; water; acetone; Amberlyst 15 at 80℃; for 10h;76%
(+/-)-trans-2-bromo-1-hydroxycyclooctane
1502-14-3, 74305-06-9, 84402-56-2

(+/-)-trans-2-bromo-1-hydroxycyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Ambient temperature; Irradiation;76%
With di-tert-butyl diperoxyoxalate In cyclohexane Heating;93 % Chromat.
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

B-methoxyborocane
60579-50-2

B-methoxyborocane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
74%
In not given IR, PMR, mass spectral data, GLC;;74%
(Pyrrolidinylmethylene)cyclooctane
76902-54-0

(Pyrrolidinylmethylene)cyclooctane

cycloactanone
502-49-8

cycloactanone

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid In diethyl ether at 25℃; for 1h;73%
Cyclooctene oxide
286-62-4

Cyclooctene oxide

A

cycloactanone
502-49-8

cycloactanone

B

cycloheptanecarboxaldehyde
4277-29-6

cycloheptanecarboxaldehyde

Conditions
ConditionsYield
at 600℃;A 71%
B 14%
With aluminum oxide; lithium bromide at 180℃; for 0.5h; Yield given. Yields of byproduct given;
(E)-1-trimethylsilyloxy-1-cyclooctene
50338-42-6

(E)-1-trimethylsilyloxy-1-cyclooctene

A

cycloactanone
502-49-8

cycloactanone

B

2-hydroxycylooctanone
496-82-2

2-hydroxycylooctanone

Conditions
ConditionsYield
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In dichloromethane for 6h; Heating;A 14%
B 71%
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In dichloromethane at 20℃; for 16h; oxidative cleavage;A 20 % Chromat.
B 45 % Chromat.
cycloactanone
502-49-8

cycloactanone

cyclooctanone oxime
1074-51-7

cyclooctanone oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol at 90 - 100℃; for 2h;100%
With ammonium chloride; Amberlyst A-21 In ethanol for 1h; Ambient temperature;95%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;90%
cycloactanone
502-49-8

cycloactanone

cyclooctanol
696-71-9

cyclooctanol

Conditions
ConditionsYield
With aluminum oxide; sodium tetrahydroborate In hexane at 30℃; for 3h;100%
With hydrogen In ethanol at 130℃; under 30003 Torr; for 20h; Autoclave;97%
With chloro-trimethyl-silane; calcium hydride; zinc(II) chloride In tetrahydrofuran at 40℃; for 0.5h;92%
cycloactanone
502-49-8

cycloactanone

2-chlorocyclooctanone
4828-34-6

2-chlorocyclooctanone

Conditions
ConditionsYield
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
100%
With ammonium cerium(IV) nitrate at 25 - 28℃; for 5.5h;86%
With p-toluenesulfonyl chloride; lithium diisopropyl amide In tetrahydrofuran -78 deg C to room t., 1 h;69%
cycloactanone
502-49-8

cycloactanone

methyl iodide
74-88-4

methyl iodide

2-methylcyclooctanone
10363-27-6

2-methylcyclooctanone

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃;100%
Stage #1: cycloactanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 0.666667h;
62%
With sodium amide
With lithium diisopropyl amide 1.) THF, -78 deg C, 30 min, 2.) THF, RT, 40 h; Yield given. Multistep reaction;
Stage #1: cycloactanone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; Further stages.;
cycloactanone
502-49-8

cycloactanone

1-chloroethyl p-tolyl sulfoxide
50635-71-7, 50635-72-8, 31350-93-3

1-chloroethyl p-tolyl sulfoxide

1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclooctanol
159763-14-1

1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-1-cyclooctanol

Conditions
ConditionsYield
at -70℃;100%
With n-butyllithium; diisopropylamine In tetrahydrofuran at -65℃; for 0.416667h;37%
cycloactanone
502-49-8

cycloactanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

cyclooctanone p-tolylsulfonylhydrazone
2567-85-3

cyclooctanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In ethanol at 100℃; for 1h;100%
In ethanol at 100℃; for 1.66667h; Inert atmosphere;100%
In methanol at 20℃; Schlenk technique;100%
cycloactanone
502-49-8

cycloactanone

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 2-oxocyclooctanecarboxylate
5452-73-3

methyl 2-oxocyclooctanecarboxylate

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane at 90℃; Reflux;100%
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 5 - 10℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran for 4.5h; Reflux; Inert atmosphere;
88%
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 5 - 10℃; for 0.5h;
Stage #2: cycloactanone In tetrahydrofuran for 4.5h; Reflux;
88%
cycloactanone
502-49-8

cycloactanone

acrolein
107-02-8

acrolein

2-(2-propen-1-ol)cyclooctanone
916853-97-9

2-(2-propen-1-ol)cyclooctanone

Conditions
ConditionsYield
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃; Further stages.;
100%
98%
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃; for 0.0166667h;
Stage #1: cycloactanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: acrolein In tetrahydrofuran; hexane at -78℃;
cycloactanone
502-49-8

cycloactanone

Bromoform
75-25-2

Bromoform

1-(Tribromomethyl)cyclooctan-1-ol
258504-47-1

1-(Tribromomethyl)cyclooctan-1-ol

Conditions
ConditionsYield
Stage #1: Bromoform With lithium diisopropyl amide In tetrahydrofuran; hexane at -100℃; for 0.166667h; Metallation;
Stage #2: cycloactanone With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether; hexane at -90℃; for 4h; Addition;
100%
cycloactanone
502-49-8

cycloactanone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

N'-cyclooctylidene-hydrazinecarboxylic acid tert-butyl ester
339058-79-6

N'-cyclooctylidene-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
In methanol at 20℃;100%
cycloactanone
502-49-8

cycloactanone

3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester
124476-10-4

3-amino-4-cyano-5-methylsulfanyl-1H-pyrrole-2-carboxylic acid ethyl ester

8-amino-6-methylsulfanyl-2,5-diaza-tricylo[7.6.0.03,7]-pentadeca-1,3,6,8-tetraene-4-carboxylic acid ethyl ester

8-amino-6-methylsulfanyl-2,5-diaza-tricylo[7.6.0.03,7]-pentadeca-1,3,6,8-tetraene-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane at 115 - 120℃; for 2h; Friedlaender cyclization reaction;100%
cycloactanone
502-49-8

cycloactanone

C32H60BO4(1-)*Na(1+)

C32H60BO4(1-)*Na(1+)

Conditions
ConditionsYield
With sodium tetrahydroborate at 60℃; for 0.5h; Ball milling; neat (no solvent); regiospecific reaction;100%
cycloactanone
502-49-8

cycloactanone

5-fluorouridine
316-46-1

5-fluorouridine

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclooctane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione

5-fluoro-1-[(3a'R,4'R,6'R,6a'R)-3a',4',6',6a'-tetrahydro-6'-(hydroxymethyl)spiro[cyclooctane-1,2'-furo[3,4-d][1,3]dioxol]-4'-yl]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4h;100%
cycloactanone
502-49-8

cycloactanone

3-(4-fluorophenyl)-3-oxopropionitrile
4640-67-9

3-(4-fluorophenyl)-3-oxopropionitrile

4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone
132812-72-7

4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazolium tetrafluoroborate at 120℃; for 1h;99.8%
With methanesulfonic acid; phosphorus pentoxide at 50℃; for 15h;95%
With PPA Heating;64%
With phosphoric acid; toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; Large scale;54%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

cycloactanone
502-49-8

cycloactanone

(cyclooct-1-enyloxy)-trimethylsilane
50338-42-6

(cyclooct-1-enyloxy)-trimethylsilane

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; Inert atmosphere;99%
With triethylamine In N,N-dimethyl-formamide for 15h; Reflux;93%
With triethylamine In N,N-dimethyl-formamide
cycloactanone
502-49-8

cycloactanone

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile
50361-50-7

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile

Conditions
ConditionsYield
With C29H46LaN3Si2 at 15℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;99%
With n-butyllithium In tetrahydrofuran; hexane for 2h; Ambient temperature;96.7%
potassium-exchanged zirconium hydrogen phosphate In dichloromethane for 20h; Heating;95%
cycloactanone
502-49-8

cycloactanone

N,N-dimethyl(methylene)ammonium chloride
30354-18-8

N,N-dimethyl(methylene)ammonium chloride

2-(Dimethylamino)methylcyclooctan-1-one
28118-62-9

2-(Dimethylamino)methylcyclooctan-1-one

Conditions
ConditionsYield
In acetonitrile for 72h; Ambient temperature;99%
cycloactanone
502-49-8

cycloactanone

potassium terbutylate

potassium terbutylate

cycloheptanone
502-42-1

cycloheptanone

A

α-(α'-cycloheptenyl)-β-hydroxycarbonyl-ethyl propionate
187819-58-5

α-(α'-cycloheptenyl)-β-hydroxycarbonyl-ethyl propionate

B

2,4,5,6,7,8-hexahydroazulene
32405-96-2

2,4,5,6,7,8-hexahydroazulene

Conditions
ConditionsYield
With hydrogenchloride In water; N,N-dimethyl-formamideA 99%
B n/a
cycloactanone
502-49-8

cycloactanone

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile
50361-50-7

1-((trimethylsilyl)oxy)cyclooctanecarbonitrile

Conditions
ConditionsYield
n-butyllithium In tetrahydrofuran99%
potassium cyanide

potassium cyanide

cycloactanone
502-49-8

cycloactanone

1,3-diazaspiro[4.7]dodecane-2,4-dione
710-94-1

1,3-diazaspiro[4.7]dodecane-2,4-dione

Conditions
ConditionsYield
Stage #1: potassium cyanide; cycloactanone In ethanol; water at 60℃; for 11h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water at 0℃; for 15h;
99%
With ammonium carbonate In methanol; water at 140℃; for 0.133333h; Sealed vial; Microwave irradiation;85%
cycloactanone
502-49-8

cycloactanone

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-((trimethylsilyl)ethynyl)cyclooctanol
1403824-58-7

1-((trimethylsilyl)ethynyl)cyclooctanol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
99%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran; hexane at 0 - 25℃; for 2h; Inert atmosphere;
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cycloactanone In tetrahydrofuran; hexane at 20℃; for 2h;
cycloactanone
502-49-8

cycloactanone

octane-1,8-dioic acid
505-48-6

octane-1,8-dioic acid

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;98%
With dihydrogen peroxide In water; acetonitrile at 90℃; for 11h; Green chemistry;92%
With dihydrogen peroxide; ortho-tungstic acid In water at 90℃; for 20h;85%
cycloactanone
502-49-8

cycloactanone

cyclooctane-1,2-dione
3008-37-5

cyclooctane-1,2-dione

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In tetrahydrofuran at 20℃; for 0.2h;98%
With perchloric acid; tripropylammonium fluorochromate (VI) In water; acetic acid at 24.9℃; Rate constant; Thermodynamic data; ΔH(activ.), ΔS(activ.), ΔG(activ.); further temperatures (308-328 K);
With selenium(IV) oxide In ethanol
furan
110-00-9

furan

cycloactanone
502-49-8

cycloactanone

1-(furan-2-yl)cyclooctanol
115754-91-1

1-(furan-2-yl)cyclooctanol

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #2: cycloactanone In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water
98%
With n-butyllithium; toluene-4-sulfonic acid Multistep reaction;
Stage #1: furan With n-butyllithium In diethyl ether; hexane at 0℃;
Stage #2: cycloactanone In diethyl ether; hexane at 0 - 20℃;
cycloactanone
502-49-8

cycloactanone

trimethylsulfoxonium bromide

trimethylsulfoxonium bromide

1-oxaspiro[2,7]-decane
185-88-6

1-oxaspiro[2,7]-decane

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 60℃; for 3h;98%
cycloactanone
502-49-8

cycloactanone

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2-hydroxymethylenecyclooctan-1-one sodium salt

2-hydroxymethylenecyclooctan-1-one sodium salt

Conditions
ConditionsYield
With ethanol; sodium In diethyl ether98%
With ethanol; sodium In diethyl ether at 20℃; for 48h; Inert atmosphere;

502-49-8Relevant articles and documents

Oxidations of secondary alcohols to ketones using easily recyclable bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF 2)n-1I(OCOCF3)2

Tesevic, Verona,Gladysz

, p. 7433 - 7440 (2006)

Reactions of commercial fluorous alkyl iodides RfnI (1-R fn; Rfn = CF3(CF2)n-1; n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOC

Metal complexes of a tetraazacyclotetradecane bearing highly fluorinated tails: New catalysts for the oxidation of hydrocarbons under fluorous biphasic conditions

Pozzi, Gianluca,Cavazzini, Marco,Quici, Silvio,Fontana, Simonetta

, p. 7605 - 7608 (1997)

The commercially available macrocycle tetraazacyclotetradecane (cyclam) has been converted into the fluorocarbon soluble ligand 1 by N-functionalization with R(F)CH2OCH2CH2OTs 3, wherein R(F) is a (per)fluorooxyalkylenic c

-

Friess,Boekelheide

, p. 4145 (1949)

-

Novel iron porphyrin-alkanethiolate complex with intramolecular NH···S hydrogen bond: Synthesis, spectroscopy, and reactivity [3]

Suzuki, Noriyuki,Higuchi, Tsunehiko,Urano, Yasuteru,Kikuchi, Kazuya,Uekusa, Hidehiro,Ohashi, Yuji,Uchida, Takeshi,Kitagawa, Teizo,Nagano, Tetsuo

, p. 11571 - 11572 (1999)

-

Iron catalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen: A synthetic metalloporphyrin as a biomimetic NAD(P)H oxidase

Maid, Harald,Boehm, Philipp,Huber, Stefan M.,Bauer, Walter,Hummel, Werner,Jux, Norbert,Groeger, Harald

, p. 2397 - 2400 (2011)

(Figure Presented) An enzyme substitute: A synthetic FeIII porphyrin was used as a catalyst for the activation and reduction of O 2 into H2O with the cofactor NAD(P)H in aqueous solution. The catalyst is compatible with different preparative enzymatic oxidation reactions. Thus, a new method is provided for the in situ regeneration of the oxidized cofactor NAD(P)+ with help from a nonenzymatic, synthetic catalyst (see scheme).

Reaction of aldehydes with the H5PV2Mo10O40 polyoxometalate and cooxidation of alkanes with molecular oxygen

Khenkin, Alexander M.,Rosenberger, Avi,Neumann, Ronny

, p. 82 - 91 (1999)

The oxidation of alkalies with molecular oxygen using aldehydes as reducing agents (aldehydes are cooxidized) was studied using the α-H5PV2Mo10O40 polyoxometalate as catalyst. Emphasis was placed on the initiation of the radical chain reaction by investigation of the aldehyde-polyoxometalate interaction. Using 31P NMR and ESR spectroscopy one could differentiate between the reactivity of the five inseparable isomers of α-H5PV2Mo10O40. Contrary to previous belief, the 1,11 isomer with vanadium in distal positions is the most abundant. The 31P NMR and ESR spectra supported by UV-vis absorption-time profiles of the reduction of α-H5PV2Mo10O40 indicated that isomers with vanadium in vicinal positions were most kinetically viable in the alkane oxidation. Addition of isobutyraldehyde to α-H5PV2Mo10O40 gave in the 51V NMR spectrum a new downfield peak attributed to the formation of an aldehyde-polyoxometalate intermediate. The alkane/aldehyde/O2 oxidizing system was found to be quite effective and selective for ketone formation. Reaction probes indicated that acyl peroxo radicals were the active oxidizing intermediates. Five pathways for its reaction were identified: chain propagation, alkane oxidation, decomposition to form oxygen, decomposition to acyl oxo radicals leading to CO2 and ketone, and capture and inhibition by the polyoxometalate.

Templating an N-heterocyclic carbene (NHC)-cyclometalated Cp?IrIII-based oxidation precatalyst on a pendant coordination platform: Assessment of the oxidative behavior via electrochemical, spectroscopic and catalytic probes

Gupta, Suraj K.,Choudhury, Joyanta

, p. 1233 - 1239 (2015)

The coordination of metalloligands to derive modified properties of the metal functionality is one of the interesting strategies practiced in materials chemistry and catalysis. In this work, a pendant terpyridine ligand has been utilized for templating a Cp?IrIII(NHC)-based (NHC = N-heterocyclic carbene) oxidation precatalyst to assess its modified oxidative behavior via electrochemical, UV-vis spectroscopic, and catalytic probes. These studies suggested that the coordination-template enhances the electron-deficiency at the IrIII redox center and affects the nature of the oxidized high-valent Ir-oxo species during chemical oxidation. Moreover, both the premodified and postmodified Cp?IrIII(NHC)-based complexes were found to be equally efficient in catalytic sp3 C-H oxidation reactions with NaIO4 as a mild sacrificial oxidant.

Simple soluble Bi(iii) salts as efficient catalysts for the oxidation of alkanes with H2O2

Rocha, Bruno G. M.,Kuznetsov, Maxim L.,Kozlov, Yuriy N.,Pombeiro, Armando J. L.,Shul'Pin, Georgiy B.

, p. 2174 - 2187 (2015)

A simple catalytic system based on a soluble bismuth(iii) salt, Bi(NO3)3/H2O2/HNO3/CH3CN + H2O, exhibits pronounced activity towards the homogeneous oxidation of inert alkanes with the yield of oxygenate products up to 32% and TON up to 112. The experimental selectivity parameters and kinetic data together with theoretical DFT calculations indicate that the reaction occurs via a free radical mechanism involving the formation of the HO radicals which directly react with alkane molecules. The mechanism of the HO generation (which is the rate limiting step of the whole process) includes the substitution of a water ligand for H2O2 in the initial aqua complex [Bi(H2O)8]3+, hydrolysis of the coordinated H2O2, second H2O-for-H2O2 substitution and the homolytic HO-OH bond cleavage in complex [Bi(H2O)4(H2O2)(OOH)]2+ (6). The relatively low overall activation energy for this process (ca. 20 kcal mol-1) is accounted for by the high lability and acidity of the Bi aqua complexes and tremendous activation of coordinated H2O2 in 6 towards homolysis. This journal is

Efficient catalytic cycloalkane oxidation employing a "helmet" phthalocyaninato iron(III) complex

Brown, Elizabeth S.,Robinson, Jerome R.,McCoy, Aaron M.,McGaff, Robert W.

, p. 5921 - 5925 (2011)

We have examined the catalytic activity of an iron(III) complex bearing the 14,28-[1,3-diiminoisoindolinato]phthalocyaninato (diiPc) ligand in oxidation reactions with three substrates (cyclohexane, cyclooctane, and indan). This modified metallophthalocyaninato complex serves as an efficient and selective catalyst for the oxidation of cyclohexane and cyclooctane, and to a far lesser extent indan. In the oxidations of cyclohexane and cyclooctane, in which hydrogen peroxide is employed as the oxidant under inert atmosphere, we have observed turnover numbers of 100.9 and 122.2 for cyclohexanol and cyclooctanol, respectively. The catalyst shows strong selectivity for alcohol (vs. ketone) formation, with alcohol to ketone (A/K) ratios of 6.7 and 21.0 for the cyclohexane and cyclooctane oxidations, respectively. Overall yields (alcohol + ketone) were 73% for cyclohexane and 92% for cyclooctane, based upon the total hydrogen peroxide added. In the catalytic oxidation of indan under similar conditions, the TON for 1-indanol was 10.1, with a yield of 12% based upon hydrogen peroxide. No 1-indanone was observed in the product mixture.

V(iv), Fe(ii), Ni(ii) and Cu(ii) complexes bearing 2,2,2-tris(pyrazol-1-yl)ethyl methanesulfonate: Application as catalysts for the cyclooctane oxidation

Silva, Telma F. S.,Rocha, Bruno G. M.,Guedes Da Silva, M. Fátima C.,Martins, Luísa M. D. R. S.,Pombeiro, Armando J. L.

, p. 528 - 537 (2016)

Water-soluble compounds [VOCl2{CH3SO2OCH2C(pz)3}] (pz = pyrazol-1-yl) 1, [FeCl2{CH3SO2OCH2C(pz)3}] 2, [NiCl2{CH3SO2OCH2C(pz)3}] 3 and [Cu{CH3SO2OCH2C(pz)3}2](OTf)24 were obtained by reactions between the corresponding metal salts and 2,2,2-tris(pyrazol-1-yl)ethyl methanesulfonate, CH3SO2OCH2C(pz)3. They were isolated as air-stable solids and fully characterized by IR, FTIR, NMR (for 2), EPR (for 1), ESI-MS(+/-), elemental analysis and (for 4) single-crystal X-ray diffraction. In all, half- (1-3) or full-sandwich (4), compounds the C-scorpionate ligand shows the N,N,N-coordination mode. 3 and 4 appear to provide the first examples of a Ni(ii) and a full-sandwich Cu(ii) compound respectively, bearing that scorpionate ligand. Compound 3 is the first Ni(ii) tris(pyrazol-1-yl)methane type complex to be applied as catalyst for the oxidation of alkanes. Compounds 1-4 exhibit catalytic activity for the peroxidative (with aq. H2O2) oxidation, in water/acetonitrile medium and under mild homogeneous conditions, of cyclooctane to the corresponding alcohol and ketone (yields up to ca. 27%). The effect of the presence of additives, such as nitric acid or pyridine, was studied.

-

Stoll,Rouve

, p. 1570,1578, 1579, 1582 (1944)

-

Hydrogen Peroxide Oxygenation of Alkanes catalysed by Manganese(III)-tetraarylporphyrins: the Remarkable Co-catalytic Effect of Lipophilic Carboxylic Acids and Heterocyclic Bases

Banfi, Stefano,Maiocchi, Alessandro,Moggi, Alberto,Montanari, Fernando,Quici, Silvio

, p. 1794 - 1796 (1990)

Oxygenation of alkanes promoted by 30percent H2O2 and catalysed by chemically robust manganese(III)-tetraaryl porphyrins 2-4 is strongly accelerated by addition of small amounts of lipophilic carboxylic acids and lipophilic heterocyclic bases; cycloalkanes are converted into mixtures of alcohols and ketones at a rate of up to 125 turnovers min-1 in CH2Cl2-H2O solution at 0 deg C.

Oxidation of alkanes catalyzed by manganese(III) porphyrin in anionic liquid at room temprature

Li, Zhen,Xia, Chun-Gu,Xu, Chuan-Zhi

, p. 9229 - 9232 (2003)

Efficient oxidation of alkanes is achieved by using an electron-deficient manganese(III) porphyrin catalyst in combination with iodobenzene diacetate in an ionic liquid at room temperature; a high-valent manganese-oxo porphyrin complex (MnV=O) was considered as the reactive oxidation intermediate.

Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles

Samani, Mahnaz,Ardakani, Mehdi Hatefi,Sabet, Mohammad

, p. 1481 - 1494 (2022/01/22)

The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4

Cu6- And Cu8-Cage Sil- And Germsesquioxanes: Synthetic and Structural Features, Oxidative Rearrangements, and Catalytic Activity

Astakhov, Grigorii S.,Levitsky, Mikhail M.,Zubavichus, Yan V.,Khrustalev, Victor N.,Titov, Aleksei A.,Dorovatovskii, Pavel V.,Smol'Yakov, Alexander F.,Shubina, Elena S.,Kirillova, Marina V.,Kirillov, Alexander M.,Bilyachenko, Alexey N.

, p. 8062 - 8074 (2021/05/26)

This study reports intriguing features in the self-assembly of cage copper(II) silsesquioxanes in the presence of air. Despite the wide variation of solvates used, a series of prismatic hexanuclear Cu6 cages (1-5) were assembled under mild conditions. In turn, syntheses at higher temperatures are accompanied by side reactions, leading to the oxidation of solvates (methanol, 1-butanol, and tetrahydrofuran). The oxidized solvent derivatives then specifically participate in the formation of copper silsesquioxane cages, allowing the isolation of several unusual Cu8-based (6 and 7) and Cu6-based (8) complexes. When 1,4-dioxane was applied as a reaction medium, deep rearrangements occurred (with a total elimination of silsesquioxane ligands), causing the formation of mononuclear copper(II) compounds bearing oxidized dioxane fragments (9 and 11) or a formate-driven 1D coordination polymer (10). Finally, a "directed"self-assembly of sil- and germsesquioxanes from copper acetate (or formate) resulted in the corresponding acetate (or formate) containing Cu6 cages (12 and 13) that were isolated in high yields. The structures of all of the products 1-13 were established by single-crystal X-ray diffraction, mainly based on the use of synchrotron radiation. Moreover, the catalytic activity of compounds 12 and 13 was evaluated toward the mild homogeneous oxidation of C5-C8 cycloalkanes with hydrogen peroxide to form a mixture of the corresponding cyclic alcohols and ketones.

Three metal centers (Co _AOMARKENCODEAMPX0AOA) Cu _AOMARKENCODEAMPX0AOA Method using Zn) 2D MOFs/ultraviolet light to catalyze oxidation of cycloalkane

-

Paragraph 0028; 0079-0080, (2021/11/06)

The invention relates to a three-metal center (Co _AOMARKENCODEAMPX0AOA). Cu _AOMARKENCODEAMPX0AOA The method comprises Zn) 2D MOFs/ultraviolet light catalytic oxidation of cycloalkane to synthesize cycloalkyl alcohol and cycloalkanone, and belongs to the field of industrial catalysis and fine organic synthesis. To the application method, metalloporphyrin three-metal center (Co _AOMARKENCODEAMPX0AOA) is used. Cu _AOMARKENCODEAMPX0AOA Zn) 2D MOFs dispersed in cycloalkane, wherein metalloporphyrin three-metal center (Co _AOMARKENCODEAMPX0AOA) Cu _AOMARKENCODEAMPX0AOA Zn) 2D MOFs mass is 0.01% - 20%, g / mol of the substance of the cycloalkane, and the reaction system is sealed. An oxidant is introduced, the ultraviolet lamp is a light source, and the reaction liquid of the stirring reaction 2.0-24 . 0h. is subjected to post-treatment to obtain the product cycloalkyl alcohol and cycloalkyl ketone. The method provided by the invention has the advantages of low reaction temperature, mild reaction conditions, high reaction efficiency, high selectivity of cycloalkyl alcohol and cycloalkyl ketone, less byproducts and small environmental impact. The invention provides a high efficiency. Available, safe cycloalkanes selectively catalyze the oxidative synthesis of cycloalkyl alcohols and cycloalkyl ketones.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 502-49-8