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Synthetic route

: 80893-84-1
1,7-bis(trimethylsiloxy)bicyclo[5.1.0]octane

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With iron(III) chloride In N,N-dimethyl-formamide at 60℃; for 16h;	73%
With iron(III) chloride In N,N-dimethyl-formamide at 60 - 70℃; for 3.25h;
With iron(III) chloride In N,N-dimethyl-formamide at 60℃;

: 57260-84-1
9-oxabicyclo[6.1.0]nonan-2-one

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In toluene at 140℃; for 96h;	52%
With 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate); tetrakis(triphenylphosphine) palladium(0) In toluene at 140℃; for 96h;	52%

: 78743-58-5
2-Hydroxy-2-methoxymethyl-cycloheptanone

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With potassium hydrogensulfate at 170 - 180℃; under 20 - 25 Torr;	51%

: 23202-10-0
(Z)-cyclooct-2-enone

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; sodium tetrachloropalladate(II) In water; isopropyl alcohol at 50℃; Wacker-Tsuji oxidation; Inert atmosphere;	37%

: 50338-48-2
1-Trimethylsiloxy-bicyclo[5.1.0]octan

A: 37996-43-3
3-hydroxycyclooctan-1-one

B: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With bis(acetylacetonate)oxovanadium; oxygen In ethanol Ambient temperature;	A 31% B 33%
With vanadyl acetylacetonate; oxygen In ethanol at 20℃; for 20h;	A 31% B 33%

: 291273-22-8
cis-cyclooctane-1,3-diol

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With chromium(VI) oxide In acetone

: 6498-54-0
1-Chlor-3-brom-cycloocten-(1)

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multistep reaction;

: 6518-11-2
1-Brom-cyclooct-1-en-3-on

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
(i) Mor, (ii) aq. HCl; Multistep reaction;

: 19719-90-5
1,2-Bis-(trimethylsiloxy)-cyclohepten-(1)

: 75-25-2
Bromoform

Et2Zn: Et2Zn

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
solvent: toluene, 0 grad C, 1 hr.; Yield given. Multistep reaction;

...Expand

trans-cyclooctane-1,3-diol: trans-cyclooctane-1,3-diol

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With chromium(VI) oxide

: 1,4-dioxa-spiro[4.7]dodecan-7-one

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
With sulfuric acid In diethyl ether; chloroform

: 1728-26-3
(Z)-1,4-dioxaspiro[4.7]dodec-6-ene

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 9-BBN / tetrahydrofuran / 48 h / 20 °C 1.2: 76 percent / NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 1 h / Heating 2.1: oxalyl chloride; DMSO; Et3N / CHCl3 / 1 h / -78 - -10 °C 3.1: H2SO4 / diethyl ether; CHCl3 View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 2: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme

: 685109-33-5
1,4-dioxaspiro[4,7]dodecan-7-ol

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl chloride; DMSO; Et3N / CHCl3 / 1 h / -78 - -10 °C 2: H2SO4 / diethyl ether; CHCl3 View Scheme

: 19719-90-5
1,2-Bis-(trimethylsiloxy)-cyclohepten-(1)

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Et2Zn / toluene / 2.25 h / Ambient temperature 2: FeCl3 / dimethylformamide / 3.25 h / 60 - 70 °C View Scheme
Multi-step reaction with 2 steps 1: 97 percent / diethylzinc / toluene / 16 h / Ambient temperature 2: 73 percent / FeCl3 / dimethylformamide / 16 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 48 percent / Zn/Cu-(CH3)2CHI / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h 2: 51 percent / potassium hydrogen sulfate / 170 - 180 °C / 20 - 25 Torr View Scheme
Multi-step reaction with 2 steps 1: diethylzinc / toluene 2: iron(III) chloride / N,N-dimethyl-formamide / 60 °C View Scheme

: 1732-08-7
dimethyl 1,7-heptanedioate

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na sand / toluene / Heating 2: Et2Zn / toluene / 2.25 h / Ambient temperature 3: FeCl3 / dimethylformamide / 3.25 h / 60 - 70 °C View Scheme

: 2050-20-6
diethyl pimelate

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / Na / toluene / 96 h / Heating 2: 97 percent / diethylzinc / toluene / 16 h / Ambient temperature 3: 73 percent / FeCl3 / dimethylformamide / 16 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: Na / toluene / 96 h 2: solvent: toluene, 0 grad C, 1 hr. View Scheme

: cis-Cyclooctyl-1,3-diacetat

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: CrO3 / acetone View Scheme

: 931-88-4, 931-87-3
(Z)-Cyclooctene

<(η5-C5H5)Fe(CO)2(CH2OSi(CH3)3)>: <(η5-C5H5)Fe(CO)2(CH2OSi(CH3)3)>

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: Br2 / CCl4 2: Mor / toluene / Heating 3: NBS, AIBN, CaCO3 / CCl4 4: acetic acid 5: KOH / methanol / Ambient temperature 6: NBS, Py / CCl4 / Heating 7: (i) Mor, (ii) aq. HCl View Scheme

: 502-49-8
cycloactanone

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: PCl3, benzene-1,2-diol / Heating 2: NBS, AIBN, CaCO3 / CCl4 View Scheme
Multi-step reaction with 5 steps 1: hydrogenchloride; bromine / ethanol; water / 72 h / 0 °C / Inert atmosphere 2: toluene-4-sulfonic acid / benzene / 24 h / Reflux; Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 4: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 5: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 3 steps
1: PCl3, benzene-1,2-diol / Heating
2: NBS, AIBN, CaCO3 / CCl4
View Scheme

Multi-step reaction with 5 steps
1: hydrogenchloride; bromine / ethanol; water / 72 h / 0 °C / Inert atmosphere
2: toluene-4-sulfonic acid / benzene / 24 h / Reflux; Inert atmosphere
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere
4: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere
5: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere
View Scheme

: 61815-42-7
(E)-1-Bromo-cyclooctene

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: NBS, AIBN, CaCO3 / CCl4 2: acetic acid 3: KOH / methanol / Ambient temperature 4: NBS, Py / CCl4 / Heating 5: (i) Mor, (ii) aq. HCl View Scheme

: 29974-69-4
1,2-dibromocyclooctane

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Mor / toluene / Heating 2: NBS, AIBN, CaCO3 / CCl4 3: acetic acid 4: KOH / methanol / Ambient temperature 5: NBS, Py / CCl4 / Heating 6: (i) Mor, (ii) aq. HCl View Scheme

: 86428-68-4
(E)-1-Chloro-cyclooctene

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NBS, AIBN, CaCO3 / CCl4 View Scheme

: 6518-10-1
1-Brom-3-hydroxy-cycloocten-(1)

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NBS, Py / CCl4 / Heating 2: (i) Mor, (ii) aq. HCl View Scheme

: 6518-05-4
1,3-Dibrom-cycloocten-(1)

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid 2: KOH / methanol / Ambient temperature 3: NBS, Py / CCl4 / Heating 4: (i) Mor, (ii) aq. HCl View Scheme

: 6518-09-8
1-Brom-3-acetoxy-cycloocten-(1)

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KOH / methanol / Ambient temperature 2: NBS, Py / CCl4 / Heating 3: (i) Mor, (ii) aq. HCl View Scheme

: 39261-18-2
2-bromocyclooctan-1-one

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / benzene / 24 h / Reflux; Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 3: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 4: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme

: 73274-50-7
2-Brom-1-cyclooctanon-ethylenacetal

: 935-29-5
1,3-cyclooctanedione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 2: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 3: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme

: 108-22-5
Isopropenyl acetate

: 935-29-5
1,3-cyclooctanedione

: 138196-40-4
1,3-diacetoxy-1,3-cyclooctadiene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 90℃;	99%

: 935-29-5
1,3-cyclooctanedione

: 74-88-4
methyl iodide

: 55277-52-6
2,2-dimethylcyclooctane-1,3-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone Ambient temperature;	97%
With potassium carbonate In N,N-dimethyl-formamide; acetone for 30h; Heating;	97%

: 75-77-4
chloro-trimethyl-silane

: 935-29-5
1,3-cyclooctanedione

: 1,3-bis-(trimethylsilyloxy)-1,3-cyclooctadiene

Conditions

Conditions	Yield
Stage #1: 1,3-cyclooctanedione With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 0℃; deprotonation; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 0℃; silylation; Further stages.;	76%
With N,N,N,N,N,N-hexamethylphosphoric triamide; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 3h;	76%

: 935-29-5
1,3-cyclooctanedione

: 1047997-32-9
2,2-difluoro-1,3-cyclooctanedione

Conditions

Conditions	Yield
With caesium carbonate; Selectfluor In acetonitrile at 0 - 20℃; Inert atmosphere;	73%
Stage #1: 1,3-cyclooctanedione With caesium carbonate In acetonitrile at 0℃; for 0.25h; Inert atmosphere; Stage #2: With Selectfluor In acetonitrile at 0 - 20℃; for 6.25h;	69%
Stage #1: 1,3-cyclooctanedione With caesium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With Selectfluor In acetonitrile at 20℃; for 1.5h; Cooling with ice; Inert atmosphere;	31.1%

: 463-51-4
Ketene

: 935-29-5
1,3-cyclooctanedione

A: 109853-13-6
Acetic acid (E)-3-oxo-cyclooct-1-enyl ester

B: 138196-40-4
1,3-diacetoxy-1,3-cyclooctadiene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 125℃; for 10h;	A 8% B 57%

...Expand

: 116-31-4
all-trans-Retinal

: 935-29-5
1,3-cyclooctanedione

: retinylidene-1,3-cyclooctanedione

Conditions

Conditions	Yield
With piperidine; acetic acid In toluene Ambient temperature;	56%

: 935-29-5
1,3-cyclooctanedione

: 100-46-9
benzylamine

: N1,N7-dibenzylheptanediamide

Conditions

Conditions	Yield
With iodine; tetrabutylammoniun azide; 4-pyrrolidin-1-ylpyridine In tetrahydrofuran at 20℃; for 12h;	51%

: 935-29-5
1,3-cyclooctanedione

: 106-93-4
ethylene dibromide

A: spiro[2.7]decane-4,10-dione

B: 3-(2-bromoethoxy)cyclooct-2-en-1-one

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 30℃; for 11.1667h;	A 24% B 14%

...Expand

: 935-29-5
1,3-cyclooctanedione

: 31465-58-4
<2,2,4,4,8,8-D6>-Cyclo-octan-1,3-dion

Conditions

Conditions	Yield
With water-d2

: 935-29-5
1,3-cyclooctanedione

: 106-47-8
4-chloro-aniline

: 6518-12-3
2-(p-Chlor-phenylhydrazono)-cyclooctandion-(1,3)

Conditions

Conditions	Yield
(i) NaNO2, aq. H2SO4, (ii) /BRN= 2354368/, NaOAc; Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 100-01-6
4-nitro-aniline

: 2-(p-Nitro-phenylhydrazono)-cyclooctandion-(1,3)

Conditions

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) /BRN= 2354368/, NaOAc; Multistep reaction;

: 16728-06-6
3-phenylbut-3-en-1-yl 4-methylbenzenesulfonate

: 935-29-5
1,3-cyclooctanedione

: 109183-23-5
3-<(3-phenyl-3-butenyl)oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 778-29-0
but-3-enyl 4-methylbenzenesulfonate

: 108162-99-8
3-(3-butenyloxy)-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 2.) DME, 60 degC, 16 h; Yield given. Multistep reaction;
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 783-86-8
4-methylpent-3-enyl 4-methylbenzenesulfonate

: 108163-02-6
3-<(4-methyl-3-pentenyl)oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 60 degC, 16 h; Yield given. Multistep reaction;
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 93652-37-0, 7515-44-8
4-phenyl-3-butenyl para-toluenesulfonate

: 108176-31-4, 109183-21-3
3-<((E)-4-phenyl-3-butenyl)oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 60 deg C, 16 h; Yield given. Multistep reaction;
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 71394-00-8
(±)-2-methylbut-3-en-1-yl 4-methylbenzenesulfonate

: 109183-18-8
3-<(2-methyl-3-butenyl)oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 36206-73-2
(E)-hexa-3,5-dien-1-yl 4-methylbenzenesulfonate

: 108163-00-4, 109183-19-9
3-<(E)-3,5-hexadienyloxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 2.) DME, 60 deg C, 16 h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 368-39-8
triethyloxonium fluoroborate

: 109183-16-6
3-(ethoxy)-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 1.) DME, 60 min, 2.) DME,CH2Cl2, 30 min; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 108162-98-7
Toluene-4-sulfonic acid (E)-5-trimethylsilanyl-pent-3-enyl ester

: 108163-03-7, 109183-26-8, 109183-27-9
3-<<(E)-5-(trimethylsilyl)-3-pentenyl>oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 87463-28-3
(Z)-hexa-3,5-dienyl p-toluenesulfonate

: 108163-00-4, 109183-19-9
3-<(E)-3,5-hexadienyloxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 109183-42-8
Toluene-4-sulfonic acid (E)-2-methyl-hexa-3,5-dienyl ester

: 109183-28-0
3-<((E)-2-methyl-3,5-hexadienyl)oxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction;

: 935-29-5
1,3-cyclooctanedione

: 100566-38-9
3-heptenyl toluenesulfonate

: 108163-01-5, 109183-20-2
3-<(E)-3-heptenyloxy>-2-cycloocten-1-one

Conditions

Conditions	Yield
With potassium tert-butylate 60 deg C, 16 h; Yield given. Multistep reaction;
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction;

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BMS 433796

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