Cis-3,5-dihydroxy-1-cyclopentene supplier

Name
Cis-3,5-dihydroxy-1-cyclopentene
EINECS
CAS No. 29783-26-4
Article Data51
CAS DataBase
Density 1.318 g/cm³
Solubility
Melting Point 56-59 °C
Formula C₅H₈O₂
Boiling Point 229.157 °C at 760 mmHg
Molecular Weight 100.117
Flash Point 113.673 °C
Transport Information
Appearance
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Cis-4-cyclopentene-1,3-diol;cis-3,5-Dihydroxy-1-cyclopenten;cis-4-Cyclopenten-1,3-diol;(1R)-2-Cyclopentene-1β,4β-diol;(1R)-4-Cyclopentene-1α,3α-diol;(1R,3S)-4-Cyclopentene-1,3-diol;(1S,3R)-4-Cyclopentene-1,3-diol;(3S)-3β,5β-Dihydroxy-1-cyclopentene;2-Cyclopentene-1β,4β-diol;
PSA 40.46000
LogP -0.33190

Synthetic route

: 542-92-7
cyclopenta-1,3-diene

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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%

: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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;

: 6573-26-8
cyclopentadiene endoperoxide

A: 16326-26-4
cis-1α,2α,4α,6α-3,7-dioxatricyclo<4.1.0.02,4>heptane

B: 29783-26-4
cis-4-cyclopentene-1,3-diol

C: 59995-47-0, 59995-49-2, 61305-27-9, 61740-29-2
4-Hydroxycyclopent-2-enone

Conditions

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%

...Expand

: 61305-33-7, 61692-07-7, 61692-08-8, 61740-30-5, 61740-31-6, 81939-24-4, 81939-25-5, 104069-09-2, 120520-91-4
cis-(+/-)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-cyclopenten-1-ol

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran for 3h; Ambient temperature;	77%

: 59995-47-0, 59995-49-2, 61305-27-9, 61740-29-2
4-Hydroxycyclopent-2-enone

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 694-47-3
trans-3,5-dihydroxycyclopent-1-ene

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at -20℃; Overall yield = 95 %;	A 71% B n/a

: 63603-17-8
(-)-2-cyclopenten-1(R),4(S)-diyl bis-N-mesyl-(S)-phenylalaninate

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With barium dihydroxide In methanol; water for 4h; Ambient temperature;	68%

: 930-60-9
maleic anhydride

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate; cerium(III) chloride In methanol	58%
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at 0℃; for 0.5h;

: 59995-47-0, 59995-49-2, 61305-27-9, 61740-29-2
4-Hydroxycyclopent-2-enone

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 6573-26-8
cyclopentadiene endoperoxide

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

B: 59995-47-0, 59995-49-2, 61305-27-9, 61740-29-2
4-Hydroxycyclopent-2-enone

Conditions

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%

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 108-03-2
1-Nitropropane

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

B: 344751-82-2
(+/-)-3-(1'-nitropropyl)cyclopentanone

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; regioselective reaction;	A 20% B 40%

...Expand

: 6573-26-8
cyclopentadiene endoperoxide

: 17356-08-0
thiourea

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 6573-26-8
cyclopentadiene endoperoxide

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With thiourea
With thiourea In dichloromethane; water

: 17040-70-9
cis-3,5-dibromocyclopentene

: 1185-59-7
tetraethylammonium acetate

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With acetone Kochen des gebildeten cis-3.5-Diacetoxy-cyclopentens-(1) in Aethanol mit methanol. Ba(OH)2-Loesung;

: 7129-41-1
6-oxabicyclo[3.1.0]hex-2-ene

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 29782-81-8
(+/-)-trans-cyclopentene-(1)-diol-(3.4)

: 694-29-1
(+/-)-cis-Cyclopent-3-ene-1,2-diol

: 694-47-3
trans-3,5-dihydroxycyclopent-1-ene

Conditions

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.

...Expand

: 542-92-7
cyclopenta-1,3-diene

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

B: 40459-97-0
cis/trans-Cyclopent-3-en-1,2-diol

: 694-47-3
trans-3,5-dihydroxycyclopent-1-ene

Conditions

Conditions	Yield
With peracetic acid; sodium acetate; sodium carbonate In dichloromethane; water; acetic acid for 1h; Ambient temperature;

...Expand

: cis-4-(trityloxy)cyclopent-2-enol

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 55℃; for 8h;	58 mg

: 61740-26-9
cis-3-acetoxy-5-hydroxycyclopent-1-ene

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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;

: 542-92-7
cyclopenta-1,3-diene

: 75-65-0
tert-butyl alcohol

1 mol H2O2: 1 mol H2O2

OsO4: OsO4

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
at 0℃;

...Expand

: 542-92-7
cyclopenta-1,3-diene

(AsCF3)4.5: (AsCF3)4.5

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 98-00-0
(2-furyl)methyl alcohol

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 61305-35-9, 61305-36-0, 61740-33-8, 56745-67-6
4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 183612-95-5
4-trityloxy-2-cyclopentenone

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 542-92-7
cyclopenta-1,3-diene

hydroxylamine hydrochloride: hydroxylamine hydrochloride

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: oxygen; rose bengal / -100 °C / Unter Belichtung 2: thiourea View Scheme

: 6573-26-8
2,3-dioxabicyclo[2.2.1]hept-5-ene

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

Conditions	Yield
With thiourea In methanol Inert atmosphere;
With thiourea In methanol; carbon dioxide Solvent; Flow reactor; liquid CO2;	94 %Spectr.

: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

A: 29783-26-4
cis-4-cyclopentene-1,3-diol

B: 60176-77-4
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

C: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

Conditions

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

...Expand

: 77-73-6, 933-60-8, 1755-01-7
bi(cyclopentadiene)

: 29783-26-4
cis-4-cyclopentene-1,3-diol

Conditions

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

: 108-05-4
vinyl acetate

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

Conditions

Conditions	Yield
With lipase from candida antartica; triethylamine In tetrahydrofuran at 20℃; for 0.5h; Enzymatic reaction; enantioselective reaction;	100%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 108-24-7
acetic anhydride

: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 4083-64-1
Tosyl isocyanate

: 138604-23-6
3-tosyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[d]oxazol-2-one

Conditions

Conditions	Yield
C36H84O12P4Pd In tetrahydrofuran Heating;	97%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 459-64-3
4-methoxybenzenediazonium tetrafluoroborate

: 3-hydroxy-4-(4-methoxyphenyl)cyclopentanone

Conditions

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%

: 1122-58-3
dmap

aqueous NaCl: aqueous NaCl

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 144-55-8
sodium hydrogencarbonate

: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

Conditions

Conditions	Yield
With pyridine; hydrogenchloride; acetic anhydride In dichloromethane	96.4%

...Expand

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 97-72-3
2-Methylpropionic anhydride

A: 161484-08-8
(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)

B: (1R,4S)-(+)-4-hydroxycyclopent-2-enyl isobutyrate

Conditions

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%

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%

...Expand

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 16326-97-9
cis-cyclopentane-1,3-diol

Conditions

Conditions	Yield
With potassium diazodicarboxylate; acetic acid In methanol at 0℃; Inert atmosphere;	94%
With hydrogen; platinum(IV) oxide

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 4-hydroxybenzenediazonium tetrafluoroborate

: 3-hydroxy-4-(4-hydroxyphenyl)cyclopentanone

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 141-75-3
butyryl chloride

: 95645-87-7
cis-Cyclopent-2-ene-1,4-diyl dibutanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 3h; Ambient temperature;	92%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 98-88-4
benzoyl chloride

: 4157-02-2
cis 2-cyclopentene 1,4-dibenzoate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	92%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 673-41-6
p-chlorobenzenediazonium tetrafluoroborate

: 3-hydroxy-4-(4-chlorophenyl)cyclopentanone

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 61692-11-3
cis-1,4-Bis(t-Butyldimethylsilyl)cyclopent-2-ene-1,4-diol

Conditions

Conditions	Yield
With pyridine; 1H-imidazole for 1.5h; Ambient temperature;	90%
With dmap; triethylamine In dichloromethane for 1h; Yield given;

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 814-49-3
diethyl chlorophosphate

: 139107-60-1
meso-4-cyclopentene-1,3-diyl bis(diethyl phosphate)

Conditions

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;

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 108-24-7
acetic anhydride

A: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

B: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

Conditions

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%

...Expand

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 79-30-1
isobutyryl chloride

: 161484-08-8
(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 3h; Ambient temperature;	87%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 79-08-3
bromoacetic acid

: 218292-26-3
((1S,4R)-4-Carboxymethoxy-cyclopent-2-enyloxy)-acetic acid

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 60℃;	86%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 492-95-5
2-methoxyphenyldiazonium tetrafluoroborate

: 3-hydroxy-4-(2-methoxyphenyl)cyclopentanone

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 2-hydroxybenzenediazonium tetrafluoroborate

: 3-hydroxy-4-(2-hydroxyphenyl)cyclopentanone

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 79-03-8
propionyl chloride

: 95645-86-6
cis-Cyclopent-2-ene-1,4-diyl dipropanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 3h; Ambient temperature;	84%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 108-23-6
isopropyl chloroformate

: 1215098-84-2
meso-cyclopent-4-ene-1,3-diyl diisopropyl dicarbonate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃;	84%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 541-41-3
chloroformic acid ethyl ester

: 188637-54-9
cyclopent-4-ene-1,3-diyl diethyl dicarbonate

Conditions

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

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: cis-3,5-cyclopent-1-ene

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane 0 deg C, 10 min; without cooling, 30 min;	80%

: 24424-99-5
di-tert-butyl dicarbonate

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 890122-43-7
carbonic acid 4-tert-butoxycarbonyloxy-cyclopent-2-enyl ester tert-butyl ester

Conditions

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%

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 673-40-5
4-bromobenzenediazonium tetrafluoroborate

: 3-hydroxy-4-(4-bromophenyl)cyclopentanone

Conditions

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%

: 108-05-4
vinyl acetate

: 29783-26-4
cis-4-cyclopentene-1,3-diol

A: 54664-61-8
cis-1,4-diacetoxy-2-cyclopentene

B: 60176-77-4
(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

Conditions

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%

...Expand

: 29783-26-4
cis-4-cyclopentene-1,3-diol

: 59995-47-0
(R)-(+)-4-hydroxy-2-cyclopentenone

Conditions

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

Cis-3,5-dihydroxy-1-cyclopentene Specification

The IUPAC name of Cis-3,5-dihydroxy-1-cyclopentene is (1S,3R)-cyclopent-4-ene-1,3-diol. With the CAS registry number 29783-26-4, it is also named as (1R)-2-Cyclopentene-1β,4β-diol. The product should be closed in a cool and dry place. In addition, its molecular formula is C₅H₈O₂ and molecular weight is 100.12.

The other characteristics of Cis-3,5-dihydroxy-1-cyclopentene can be summarized as: (1)ACD/LogP: -0.64; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 40.46 Å²; (7)Index of Refraction: 1.596; (8)Molar Refractivity: 25.843 cm³; (9)Molar Volume: 75.983 cm³; (10)Polarizability: 10.245×10^-24cm³; (11)Surface Tension: 53.022 dyne/cm; (12)Density: 1.318 g/cm³; (13)Flash Point: 113.673 °C; (14)Melting Point: 56-59 °C; (15)Enthalpy of Vaporization: 54.147 kJ/mol; (16)Boiling Point: 229.157 °C at 760 mmHg; (17)Vapour Pressure: 0.014 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES: O[C@@H]1/C=C\[C@H](O)C1
(2)InChI: InChI=1/C5H8O2/c6-4-1-2-5(7)3-4/h1-2,4-7H,3H2/t4-,5+
(3)InChIKey: IGRLIBJHDBWKNA-SYDPRGILBY
(4)Std. InChI: InChI=1S/C5H8O2/c6-4-1-2-5(7)3-4/h1-2,4-7H,3H2/t4-,5+
(5)Std. InChIKey: IGRLIBJHDBWKNA-SYDPRGILSA-N

Product Name

Cis-3,5-dihydroxy-1-cyclopentene

Synthetic route

Cis-3,5-dihydroxy-1-cyclopentene Specification

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