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CIS-3,5-DIHYDROXY-1-CYCLOPENTENEAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express
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inquirycyclopenta-1,3-diene
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With oxygen; rose bengal; thiourea In methanol at 20℃; for 12h; Irradiation; | 100% |
Stage #1: cyclopenta-1,3-diene With oxygen In dichloromethane at 20℃; for 3h; visible light irradiation; Stage #2: With thiourea | 95% |
Stage #1: cyclopenta-1,3-diene With oxygen; tetrakis(pentafluorophenyl)porphyrin In methanol; carbon dioxide under 90009 Torr; Irradiation; Flow reactor; liquid CO2; Stage #2: With thiourea In methanol; carbon dioxide at 0℃; under 90009 Torr; Flow reactor; liquid CO2; | 94% |
cis-1,4-diacetoxy-2-cyclopentene
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 0℃; for 4h; | 94% |
With potassium carbonate In methanol for 2h; Heating; | 40 g |
With sodium hydroxide In methanol; water Reflux; | |
With potassium carbonate In methanol at 0℃; for 4h; |
cyclopentadiene endoperoxide
A
cis-1α,2α,4α,6α-3,7-dioxatricyclo<4.1.0.02,4>heptane
B
cis-4-cyclopentene-1,3-diol
C
4-Hydroxycyclopent-2-enone
Conditions | Yield |
---|---|
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at -25℃; for 1h; Product distribution; ruthenium(II) catalyzed reaction of 1,4-endoperoxide; | A 78% B 3% C 5% |
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at -78 - -25℃; for 2.5h; | A 71.8% B 2.6% C 3.5% |
cis-(+/-)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclopenten-1-ol
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran for 3h; Ambient temperature; | 77% |
4-Hydroxycyclopent-2-enone
A
cis-4-cyclopentene-1,3-diol
trans-3,5-dihydroxycyclopent-1-ene
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at -20℃; Overall yield = 95 %; | A 71% B n/a |
(-)-2-cyclopenten-1(R),4(S)-diyl bis-N-mesyl-(S)-phenylalaninate
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With barium dihydroxide In methanol; water for 4h; Ambient temperature; | 68% |
maleic anhydride
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cerium(III) chloride In methanol | 58% |
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at 0℃; for 0.5h; |
4-Hydroxycyclopent-2-enone
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at -40 - 20℃; Sealed tube; | 55% |
Multi-step reaction with 3 steps 1: 36 percent / DBU / CH2Cl2 / 72 h / Ambient temperature 2: LiAlH4, LiI / toluene; various solvent(s) / 1.) -20 deg C, 1 h, 2.) -20 deg C to 0 deg C, 0.5 h, 3.) 0 deg C to 15 deg C, 4 h 3: 58 mg / p-TsOH / ethanol / 8 h / 55 °C View Scheme | |
Multi-step reaction with 3 steps 1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 2: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 3: 77 percent / Et3N, TBAF / tetrahydrofuran / 3 h / Ambient temperature View Scheme | |
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at -70 - -60℃; for 2h; | |
Stage #1: 4-Hydroxycyclopent-2-enone With cerium(III) chloride heptahydrate In tetrahydrofuran; methanol at 7℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tetrahydroborate; water; sodium hydroxide In tetrahydrofuran; methanol at -33 - -20℃; | 86 g |
cyclopentadiene endoperoxide
A
cis-4-cyclopentene-1,3-diol
B
4-Hydroxycyclopent-2-enone
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 4℃; for 20h; Mechanism; | A 16% B 54% |
tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 4℃; for 20h; | A 16% B 54% |
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
1-Nitropropane
A
cis-4-cyclopentene-1,3-diol
B
(+/-)-3-(1'-nitropropyl)cyclopentanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; regioselective reaction; | A 20% B 40% |
cyclopentadiene endoperoxide
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With thiourea | |
With thiourea In dichloromethane; water |
cis-3,5-dibromocyclopentene
tetraethylammonium acetate
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With acetone Kochen des gebildeten cis-3.5-Diacetoxy-cyclopentens-(1) in Aethanol mit methanol. Ba(OH)2-Loesung; |
6-oxabicyclo[3.1.0]hex-2-ene
A
cis-4-cyclopentene-1,3-diol
(+/-)-trans-cyclopentene-(1)-diol-(3.4)
(+/-)-cis-Cyclopent-3-ene-1,2-diol
trans-3,5-dihydroxycyclopent-1-ene
Conditions | Yield |
---|---|
With sodium perchlorate; water In acetone at 25℃; Rate constant; Mechanism; pH - rate profile; | A n/a B n/a C 25 % Chromat. D 42 % Chromat. |
cyclopenta-1,3-diene
A
cis-4-cyclopentene-1,3-diol
B
cis/trans-Cyclopent-3-en-1,2-diol
trans-3,5-dihydroxycyclopent-1-ene
Conditions | Yield |
---|---|
With peracetic acid; sodium acetate; sodium carbonate In dichloromethane; water; acetic acid for 1h; Ambient temperature; |
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 55℃; for 8h; | 58 mg |
cis-3-acetoxy-5-hydroxycyclopent-1-ene
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With methanol; potassium carbonate In diethyl ether for 4h; | |
Stage #1: cis-3-acetoxy-5-hydroxycyclopent-1-ene With tert-butyl acetoacetate; potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; |
Conditions | Yield |
---|---|
at 0℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: O2 / Nafilon-supported Pt(II) terpyridyl complex / D2O; CH2Cl2 / 20 °C / Irradiation 2: thiourea / H2O; CH2Cl2 View Scheme |
(2-furyl)methyl alcohol
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 36 percent / DBU / CH2Cl2 / 72 h / Ambient temperature 3: LiAlH4, LiI / toluene; various solvent(s) / 1.) -20 deg C, 1 h, 2.) -20 deg C to 0 deg C, 0.5 h, 3.) 0 deg C to 15 deg C, 4 h 4: 58 mg / p-TsOH / ethanol / 8 h / 55 °C View Scheme | |
Multi-step reaction with 4 steps 1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 3: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 4: 77 percent / Et3N, TBAF / tetrahydrofuran / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: potassium dihydrogenphosphate; phosphoric acid / water / 22 h / 25 - 99 °C / pH 4.1 2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C View Scheme |
4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: 77 percent / Et3N, TBAF / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
4-trityloxy-2-cyclopentenone
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4, LiI / toluene; various solvent(s) / 1.) -20 deg C, 1 h, 2.) -20 deg C to 0 deg C, 0.5 h, 3.) 0 deg C to 15 deg C, 4 h 2: 58 mg / p-TsOH / ethanol / 8 h / 55 °C View Scheme |
cyclopenta-1,3-diene
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxygen; rose bengal / -100 °C / Unter Belichtung 2: thiourea View Scheme |
2,3-dioxabicyclo[2.2.1]hept-5-ene
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With thiourea In methanol Inert atmosphere; | |
With thiourea In methanol; carbon dioxide Solvent; Flow reactor; liquid CO2; | 94 %Spectr. |
cis-1,4-diacetoxy-2-cyclopentene
A
cis-4-cyclopentene-1,3-diol
B
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
C
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
With pseudomonas fluorescens lipase In hexane; water at 25℃; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | |
With lipase B from Candida antarctica In aq. phosphate buffer at 20℃; pH=7.5; Solvent; Enzymatic reaction; | A n/a B n/a C n/a |
bi(cyclopentadiene)
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3 h / 200 - 300 °C 2: rose bengal; thiourea / methanol; isopropyl alcohol / -20 °C / Irradiation; Flow reactor View Scheme |
vinyl acetate
cis-4-cyclopentene-1,3-diol
cis-1,4-diacetoxy-2-cyclopentene
Conditions | Yield |
---|---|
With lipase from candida antartica; triethylamine In tetrahydrofuran at 20℃; for 0.5h; Enzymatic reaction; enantioselective reaction; | 100% |
cis-4-cyclopentene-1,3-diol
acetic anhydride
cis-1,4-diacetoxy-2-cyclopentene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 97% |
With triethylamine In dichloromethane for 3h; | 97% |
With dmap In pyridine; dichloromethane 1.) 0 deg C,; 2.) room temperature 13 h; | 96.4% |
cis-4-cyclopentene-1,3-diol
Tosyl isocyanate
3-tosyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[d]oxazol-2-one
Conditions | Yield |
---|---|
C36H84O12P4Pd In tetrahydrofuran Heating; | 97% |
cis-4-cyclopentene-1,3-diol
4-methoxybenzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; Catalytic behavior; Reagent/catalyst; Temperature; Heck Reaction; Sealed tube; diastereoselective reaction; | 97% |
dmap
cis-4-cyclopentene-1,3-diol
sodium hydrogencarbonate
cis-1,4-diacetoxy-2-cyclopentene
Conditions | Yield |
---|---|
With pyridine; hydrogenchloride; acetic anhydride In dichloromethane | 96.4% |
cis-4-cyclopentene-1,3-diol
2-Methylpropionic anhydride
A
(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)
Conditions | Yield |
---|---|
Stage #1: cis-4-cyclopentene-1,3-diol With (4-(pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine-2,6-diyl)bis(bis(4-((tertbutyldimethylsilyl)oxy)phenyl)methanol); N-ethyl-N,N-diisopropylamine In tert-butyl methyl ether at -40℃; for 0.25h; Stage #2: 2-Methylpropionic anhydride In tert-butyl methyl ether at -40℃; for 8h; Reagent/catalyst; Temperature; Concentration; Time; enantioselective reaction; | A 4% B 95% |
cis-4-cyclopentene-1,3-diol
cis-cyclopentane-1,3-diol
Conditions | Yield |
---|---|
With potassium diazodicarboxylate; acetic acid In methanol at 0℃; Inert atmosphere; | 94% |
With hydrogen; platinum(IV) oxide |
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; for 3h; Heck Reaction; Sealed tube; diastereoselective reaction; | 94% |
cis-4-cyclopentene-1,3-diol
butyryl chloride
cis-Cyclopent-2-ene-1,4-diyl dibutanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Ambient temperature; | 92% |
cis-4-cyclopentene-1,3-diol
benzoyl chloride
cis 2-cyclopentene 1,4-dibenzoate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 92% |
cis-4-cyclopentene-1,3-diol
p-chlorobenzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; Catalytic behavior; Reagent/catalyst; Temperature; Heck Reaction; Sealed tube; diastereoselective reaction; | 92% |
cis-4-cyclopentene-1,3-diol
tert-butyldimethylsilyl chloride
cis-1,4-Bis(t-Butyldimethylsilyl)cyclopent-2-ene-1,4-diol
Conditions | Yield |
---|---|
With pyridine; 1H-imidazole for 1.5h; Ambient temperature; | 90% |
With dmap; triethylamine In dichloromethane for 1h; Yield given; |
cis-4-cyclopentene-1,3-diol
diethyl chlorophosphate
meso-4-cyclopentene-1,3-diyl bis(diethyl phosphate)
Conditions | Yield |
---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -40 - 0℃; | 90% |
Stage #1: cis-4-cyclopentene-1,3-diol With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h; Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -40 - 0℃; | 90% |
With pyridine; dmap at 0 - 20℃; for 10h; Inert atmosphere; | 60% |
With pyridine; dmap at 25℃; for 1h; Inert atmosphere; |
cis-4-cyclopentene-1,3-diol
acetic anhydride
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate
Conditions | Yield |
---|---|
Stage #1: cis-4-cyclopentene-1,3-diol With (4-(pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]azepine-2,6-diyl)bis(bis(4-((tertbutyldimethylsilyl)oxy)phenyl)methanol); N-ethyl-N,N-diisopropylamine In tert-butyl methyl ether at -40℃; for 0.25h; Stage #2: acetic anhydride In tert-butyl methyl ether at -40℃; for 6h; Temperature; Time; enantioselective reaction; | A n/a B 89% |
cis-4-cyclopentene-1,3-diol
isobutyryl chloride
(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Ambient temperature; | 87% |
cis-4-cyclopentene-1,3-diol
bromoacetic acid
((1S,4R)-4-Carboxymethoxy-cyclopent-2-enyloxy)-acetic acid
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 60℃; | 86% |
cis-4-cyclopentene-1,3-diol
2-methoxyphenyldiazonium tetrafluoroborate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; Heck Reaction; Sealed tube; diastereoselective reaction; | 86% |
cis-4-cyclopentene-1,3-diol
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; for 5h; Heck Reaction; Sealed tube; diastereoselective reaction; | 85% |
cis-4-cyclopentene-1,3-diol
propionyl chloride
cis-Cyclopent-2-ene-1,4-diyl dipropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; Ambient temperature; | 84% |
cis-4-cyclopentene-1,3-diol
isopropyl chloroformate
meso-cyclopent-4-ene-1,3-diyl diisopropyl dicarbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; | 84% |
cis-4-cyclopentene-1,3-diol
chloroformic acid ethyl ester
cyclopent-4-ene-1,3-diyl diethyl dicarbonate
Conditions | Yield |
---|---|
With pyridine In diethyl ether Ambient temperature; | 81% |
Stage #1: cis-4-cyclopentene-1,3-diol With pyridine In dichloromethane at 5℃; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In dichloromethane at 5 - 20℃; Inert atmosphere; | 14 g |
cis-4-cyclopentene-1,3-diol
di-tert-butylsilyl bis(trifluoromethanesulfonate)
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane 0 deg C, 10 min; without cooling, 30 min; | 80% |
di-tert-butyl dicarbonate
cis-4-cyclopentene-1,3-diol
carbonic acid 4-tert-butoxycarbonyloxy-cyclopent-2-enyl ester tert-butyl ester
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water at 0 - 20℃; for 24h; | 80% |
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 0 - 20℃; | 80% |
cis-4-cyclopentene-1,3-diol
4-bromobenzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 4,4-dimethyl-2-(quinolin-2-yl)-4,5-dihydrooxazole; zinc(II) carbonate In methanol at 40℃; for 0.5h; Heck Reaction; Sealed tube; diastereoselective reaction; | 79% |
vinyl acetate
cis-4-cyclopentene-1,3-diol
A
cis-1,4-diacetoxy-2-cyclopentene
B
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 4h; Ambient temperature; lipase from Mucor sp.; | A 10% B 78% |
With Chirazyme In acetic acid butyl ester for 12h; | A 72% B 22% |
With triethylamine In tetrahydrofuran for 2.5h; Ambient temperature; pancreatin; | A 32% B 65% |
cis-4-cyclopentene-1,3-diol
(R)-(+)-4-hydroxy-2-cyclopentenone
Conditions | Yield |
---|---|
With catalase from Micrococcus lysodeikticus; oxygen; NADP; calcium chloride In aq. phosphate buffer at 30℃; for 24h; pH=7.0; Reagent/catalyst; Enzymatic reaction; | 77% |
Multi-step reaction with 5 steps 1: pyridine / Ambient temperature 2: TsOH / tetrahydrofuran; CH2Cl2 / Ambient temperature 3: NaOH / tetrahydrofuran; H2O / 5 h / Ambient temperature 4: 80 percent / Jones reagent / acetone / 0.5 h 5: 77 percent / aq.acetic acid / 15 h / Ambient temperature View Scheme |
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