4-Cyclopentene-1,3-diol,1-acetate, (1S,3R)- supplier

Name
(1R,4S)-CIS-4-ACETOXY-2-CYCLOPENTEN-1-OL
EINECS
CAS No. 60176-77-4
Article Data43
CAS DataBase
Density 1.171 g/cm³
Solubility
Melting Point 49-51 °C
Formula C₇H₁₀O₃
Boiling Point 207.984 °C at 760 mmHg
Molecular Weight 142.155
Flash Point 83.718 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Cyclopentene-1,3-diol, monoacetate, (1R,3S)-;
PSA 46.53000
LogP 0.23890

Synthetic route

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

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

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

Conditions

Conditions	Yield
With methanol; lipase B from Candida antarctica In tert-butyl methyl ether at 5℃; for 16h; Enzymatic reaction; enantioselective reaction;	A n/a B 95%
With sodium hydroxide; Esterase(porcine liver)PLE In water at 32℃; for 8h; Product distribution; further enzymes; pH=7, phosphate buffer;
With N-(2-acetamido)-2-aminoethanesulfonic acid; ethanolamine; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 8h; Product distribution; antibody of IgG class: 37E8, pH 8.0; Km, Kcat, Ki; var. enzymes and time;

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

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

Conditions

Conditions	Yield
With sodium hydroxide; phosphate buffer; immobilized porcine liver esterase (PLE, E. C. 3.1.1.1) on Eupergit C at 32℃; for 14h; pH= 7;	87%
With sodium hydroxide; sodium phosphate buffer; Trichosporon beigelii (NCIM 3326) In ethanol for 26h; pH=7; Hydrolysis;	74%
With Trichosporon beigelii NCIM 3326 In ethanol at 20℃; for 26h; pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;	74%

: 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

: 103729-50-6
(1R,3S)-(-)-1-acetoxycyclopentan-3-ol

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

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran	77%
With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran for 2h; Ambient temperature;	67%
With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran Inert atmosphere;	50%

: 108-05-4
vinyl acetate

: 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

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

Conditions

Conditions	Yield
lipase EC 3.1.1.3 L10 In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity;	A n/a B 76.4% C n/a
lipase EC 3.1.1.3 QLC In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity;	A n/a B 76.4% C n/a
lipase EC 3.1.1.3 QL In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity;	A n/a B 75.5% C n/a
lipase EC 3.1.1.3 QLG In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity;	A n/a B 61.9% C n/a
pancreatin lipase In water; acetone at 5 - 25℃; for 6.5h; Product distribution / selectivity;	A n/a B 16.5% C n/a

...Expand

: cis-3,5-diacetoxycyclopentene

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

Conditions

Conditions	Yield
With pig liver esterase; sodium hydroxide In aq. phosphate buffer for 19h; pH=7; Enzymatic reaction;	75%

: 108-05-4
vinyl acetate

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

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

Conditions

Conditions	Yield
With Pancreatin; triethylamine In tetrahydrofuran at 20℃; for 3h;	72%
With Pancreatin	72%
With Pancreatin; triethylamine In tetrahydrofuran; water at 5℃; for 23h;	70%

: 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

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

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 23h; Enzymatic reaction; enantioselective reaction;	A 25% B 61% C n/a

...Expand

: 108-05-4
vinyl acetate

: cis-cyclopent-4-ene-1,3-diol

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

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 22h; Enzymatic reaction;	53%

: 108-22-5
Isopropenyl 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
In various solvent(s) at 50℃; for 72h; Candida antarctica lipase B (Novo SP-435); other meso-diols; enzymatic asymmetrization of meso-2-cycloalken-1,4-diols in organic media;	A n/a B 52%
In various solvent(s) at 50℃; for 72h; Candida antarctica lipase B (Novo SP-435); Yields of byproduct given;	A n/a B 52%

...Expand

: 108-22-5
Isopropenyl acetate

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

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

Conditions

Conditions	Yield
at 50℃; acrylic supported Candida antarctica lipase B;	50%

: 625-24-1
2,2,2-trichloroethyl 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
In pyridine for 72h; Ambient temperature; porcine pancreatic lipase;	A 22% B 50%
With triethylamine In tetrahydrofuran for 5h; Ambient temperature; pancreatin;	A 45% B 48%
With triethylamine In tetrahydrofuran for 5h; Ambient temperature; pancreatin;	A 45% B 48%
With triethylamine In tetrahydrofuran for 5h; Mechanism; Ambient temperature; pancreatin; other 2,2,2-trichloroethyl alkanoates;	A 45% B 48%

...Expand

: 625-24-1
2,2,2-trichloroethyl acetate

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

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 5h; Ambient temperature; pancreatin;	A 49% B 46%

...Expand

: 108-05-4
vinyl acetate

: 4157-01-1
cis-2-cyclopentenyl-1,4-diol

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

Conditions

Conditions	Yield
With Pancreatin; triethylamine In tetrahydrofuran at 20℃; Enzymatic reaction;	14%

: 625-24-1
2,2,2-trichloroethyl acetate

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

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

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

Conditions

Conditions	Yield
pancreatin/base;

...Expand

: 95722-35-3
(1S,4R)-(-)-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenyl acetate

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

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

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

Co2(CO)8: Co2(CO)8

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / O2; thiourea; Bengal rose / methanol / 18 h / -35 - 20 °C / Irradiation 2: 72 percent / Et3N; pancreatin / tetrahydrofuran / 3 h / 20 °C View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 53 percent / KH2PO4, H3PO4 / H2O / 40 h / 99 °C / pH 4.1 2: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 3: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 4: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 5: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme
Multi-step reaction with 5 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: 48 percent / Et3N, pancreatin / various solvent(s) / 7 h / Ambient temperature 5: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 5 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: 48 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 5: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 76 percent / PPTs / tetrahydrofuran / 18 h / Ambient temperature 2: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 3: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 4: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 2: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 3: 48 percent / Et3N, pancreatin / various solvent(s) / 7 h / Ambient temperature 4: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 72 percent / Et3N, DMAP / tetrahydrofuran / Ambient temperature 2: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 3: 48 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 4: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: 48 percent / Et3N, pancreatin / various solvent(s) / 7 h / Ambient temperature 3: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: LiAlH4, LiI, TBSOH / toluene; various solvent(s) / 23 h / -30 - -25 °C 2: 48 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 3: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride; lithium iodide / toluene; tert-butyl methyl ether / 3 h / -30 °C / Inert atmosphere; Large scale 2: triethylamine; Pancreatin / tert-butyl methyl ether / 7 h / Inert atmosphere; Large scale; Enzymatic reaction 3: triethylamine; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere View Scheme

: 61305-37-1, 62356-78-9, 70615-05-3
4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enone

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4, LiI / various solvent(s); toluene / 0.5 h / -20 - -13 °C 2: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 3: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme

: 37517-41-2, 61375-54-0, 61375-55-1, 63640-56-2, 63640-57-3, 77341-50-5, 112458-81-8, 130792-62-0, 130792-63-1
(+/-)-cis-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenol

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 45 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 2: p-TsOH / ethanol / 2 h / Ambient temperature View Scheme

: 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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / Et3N, pancreatin / various solvent(s) / 7 h / Ambient temperature 2: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 48 percent / Et3N, pancreatin, vinyl acetate / various solvent(s) / 7 h / Ambient temperature 2: 67 percent / Et3N, TBAF / tetrahydrofuran / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 48 percent / Et3N / various solvent(s) / pancreatin 2: 77 percent / tetrabutylammonium fluoride, Et3N / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: triethylamine; Pancreatin / tert-butyl methyl ether / 7 h / Inert atmosphere; Large scale; Enzymatic reaction 2: triethylamine; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere View Scheme

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

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

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

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

: 60389-71-1, 60410-14-2, 61826-75-3
meso-cis-1,4-diacetoxy-2-cyclopentene

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

Conditions

Conditions	Yield
With sodium hydroxide
Multi-step reaction with 2 steps 1: potassium hydrogencarbonate / methanol / Reflux 2: triethylamine; Pancreatin / tetrahydrofuran / 20 °C / Enzymatic reaction View Scheme

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

: 64-19-7
acetic acid

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

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

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Triethylene glycol dimethyl ether In tetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Overall yield = 85 %Chromat.;	A n/a B n/a

...Expand

: 1890-04-6
3,5-cis-dibromocyclopentene

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-benzyl-N,N,N-triethylammonium chloride / tert-butyl alcohol / Reflux 2: potassium hydrogencarbonate / methanol / Reflux 3: triethylamine; Pancreatin / tetrahydrofuran / 20 °C / Enzymatic reaction View Scheme

: 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

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

: 124-63-0
methanesulfonyl chloride

: 177566-45-9
(1S,4S)-1-acetoxy-4-methanesulfonyloxy-cyclopent-2-ene

Conditions

Conditions	Yield
With triethylamine In dichloromethane 1.) 0 deg C to rt, 2.) rt, 6 h;	100%
With triethylamine In dichloromethane Ambient temperature;	100%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 103729-50-6
(1R,3S)-(-)-1-acetoxycyclopentan-3-ol

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 23℃; for 12h;	99%
With 1H-imidazole In dichloromethane	90%
With 1H-imidazole In N,N-dimethyl-formamide

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

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 1477979-57-9
(1S,4R)-1-acetyloxy-4-(4-methoxyphenylmethoxy)cyclopent-2-ene

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane; pentane at 0 - 20℃; for 33h;	99%

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

: 836643-56-2
[1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane

: 836643-54-0
4-(4-(1-(t-butyldimethylsilyloxy)hexyl)phenyl)-2-cyclopenten-1-ol

Conditions

Conditions	Yield
Stage #1: [1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane With magnesium In tetrahydrofuran Stage #2: (1S,4R)-4-hydroxy-2-cyclopentenyl acetate With lithium chloride In tetrahydrofuran at 0℃; for 1h;	98%

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

: 137726-50-2
(1R,2R,4S,5S)-(-)-2-hydroxy-6-oxabicyclo<3.1.0>hex-4-yl acetate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h; Ambient temperature;	96%

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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 872624-44-7
Acetic acid (1S,4R)-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enyl ester

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	95%

: 524-38-9
N-hydroxyphthalimide

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

: 163252-33-3
(1S,4S)-trans-1-acetoxy-4-(phthalimidooxy)-2-cyclopentene

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature;	94%

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

: 100-39-0
benzyl bromide

: 183612-92-2
(1S,4R)-4-(benzyloxy)cyclopent-2-en-1-yl acetate

Conditions

Conditions	Yield
With silver(l) oxide In dichloromethane at 20℃; for 12h;	93%
With silver(l) oxide In dichloromethane at 20℃; Inert atmosphere;	47.7%
With silver(l) oxide In dichloromethane at 20℃; for 168.5h; Inert atmosphere; Darkness;	47.7%

: 3587-60-8
Benzyloxymethyl chloride

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

: 934986-74-0
(1R,4R)-4-(benzyloxymethyl)cyclopent-2-enol

Conditions

Conditions	Yield
Stage #1: Benzyloxymethyl chloride With bromine; magnesium; mercury dichloride In tetrahydrofuran at -5℃; for 2.5h; Stage #2: (1S,4R)-4-hydroxy-2-cyclopentenyl acetate In tetrahydrofuran at -20℃; for 0.25h; Further stages.;	92%

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

: 60190-78-5
methyl 2-diazo-2-(dimethoxyphosphoryl)acetate

: (+)-(1R,4S)-1-[(methoxycarbonyl)dimethyl phosphonomethoxy]-4-acetoxycyclopent-2-ene

Conditions

Conditions	Yield
With dirhodium tetraacetate In benzene for 6h; Molecular sieve; Inert atmosphere; Reflux;	92%

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

: 161029-10-3
2',2',2'-trichloroethyl (E)-3-ethoxyacrylate

: 2',2',2'-trichloroethyl (1''R,4''S)-3-(cis-4''-acetoxycyclopent-2''-enyloxy)-2-bromo-3-ethoxypropionate

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane Ambient temperature;	91%

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

: 149342-57-4
(1S,3R)-cis-3-acetoxycyclopentan-1-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate; hydrogen; nickel(II) acetate tetrahydrate In ethanol under 5171.62 Torr; for 4h; Autoclave;	87%
With hydrogen; nickel In ethanol at 15 - 20℃; under 750.06 - 3000.2 Torr; for 5h;	55%

: C6H5ClMg*CCuN

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

: 913715-19-2
(1R,4R)-4-phenylcyclopent-2-enol

Conditions

Conditions	Yield
In tetrahydrofuran Grignard reaction;	87%

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

: C15H23BrMgO2

A: 886841-24-3
(1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol

B: (1R,2R)-2-[7-(4-Methoxy-benzyloxy)-heptyl]-cyclopent-3-enol

Conditions

Conditions	Yield
Stage #1: C15H23BrMgO2 With lithium chloride In tetrahydrofuran at -10℃; for 0.5h; Stage #2: (1S,4R)-4-hydroxy-2-cyclopentenyl acetate In tetrahydrofuran at -10℃; for 3h;	A 81% B n/a

...Expand

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

: 103-71-9
phenyl isocyanate

: (1S,4R)-4-(((phenyl)carbamoyl)oxy)cyclopent-2-en-1-yl acetate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; Inert atmosphere;	81%

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

: 5416-93-3
4-Methoxyphenyl isocyanate

: (1S,4R)-4-(((4-methoxyphenyl)carbamoyl)oxy)cyclopent-2-en-1-yl acetate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 23℃; Inert atmosphere;	81%

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

: 161029-09-0
2',2'-dichloroethyl (E)-3-ethoxyacrylate

: 2',2'-dichloroethyl (1''R,4''S)-3-(cis-4''-acetoxycyclopent-2''-enyloxy)-2-bromo-3-ethoxypropionate

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane Ambient temperature;	77%

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

: 203301-80-8
2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane

A: 203301-59-1
(1R,4R,1'E,3'S)-4-[{3'-(tert-butyldimethylsilyl)oxy}-1'-octenyl]-2-cyclopenten-1-ol

B: (1R,2S)-2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopent-3-enol

Conditions

Conditions	Yield
Stage #1: 2-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-4,5-dimethyl-[1,3,2]dioxaborolane With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium; sodium iodide In tetrahydrofuran; hexane Cooling; Stage #2: (1S,4R)-4-hydroxy-2-cyclopentenyl acetate With tert-butyl isocyanide In tetrahydrofuran; hexane at 20℃; for 3h; Further stages.;	A 76% B 3.6%

...Expand

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

: 221101-01-5
4-nitro-N-(prop-2-yn-1-yl)benzene-1-sulfonamide

: Acetic acid (1S,4S)-4-[(4-nitro-benzenesulfonyl)-prop-2-ynyl-amino]-cyclopent-2-enyl ester

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h; Mitsunobu coupling;	76%

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

: 35059-50-8
t-butyl diazoacetate

: 1073136-19-2
cis-(-)-{[(1R,4S)-4-acetoxycyclopent-2-en-1-yl]oxy}acetic acid tert-butyl ester

Conditions

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 20℃; Inert atmosphere;	73.7%

: 5941-55-9
ethyl 3-ethoxyacrylate

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

: ethyl (1'R,4'S)-3-(cis-4'-acetoxycyclopent-2'-enyloxy)-2-bromo-3-ethoxypropionate

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane Ambient temperature;	72%

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

: 78681-80-8
methyl (E)-3-ethoxy-2-propenoate

: methyl (1'R,4'S)-3-(cis-4'-acetoxycyclopent-2'-enyloxy)-2-bromo-3-ethoxypropionate

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane Ambient temperature;	67%

4-Cyclopentene-1,3-diol,1-acetate, (1S,3R)- Specification

The 4-Cyclopentene-1,3-diol,1-acetate, (1S,3R)-, with the CAS registry number of 60176-77-4, is also known as 4-Cyclopentene-1,3-diol, monoacetate, (1R,3S)-. Its molecular formula is C₇H₁₀O₃ and molecular weight is 142.15. What's more, its systematic name is (1R,4S)-4-Hydroxycyclopent-2-en-1-yl acetate. In addition, it must be stored in airtight containers and placed in a dry, cool place.

Physical properties about the 4-Cyclopentene-1,3-diol,1-acetate, (1S,3R)- are: (1)ACD/LogP: -0.04; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 46.53 Å²; (7)Index of Refraction: 1.5; (8)Molar Refractivity: 35.666 cm³; (9)Molar Volume: 121.367 cm³; (10)Surface Tension: 40.837 dyne/cm; (11)Density: 1.171 g/cm³; (12)Flash Point: 83.718 °C; (13)Enthalpy of Vaporization: 51.676 kJ/mol; (14)Boiling Point: 207.984 °C at 760 mmHg; (15)Vapour Pressure: 0.051 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
As a chemical, the dust of this chemical can not be breathed. And you should avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O[C@H]1\C=C/[C@@H](O)C1)C
(2) InChI: InChI=1/C7H10O3/c1-5(8)10-7-3-2-6(9)4-7/h2-3,6-7,9H,4H2,1H3/t6-,7+/m1/s1
(3) InChIKey: IJDYOKVVRXZCFD-RQJHMYQMBY

Product Name

(1R,4S)-CIS-4-ACETOXY-2-CYCLOPENTEN-1-OL

Synthetic route

4-Cyclopentene-1,3-diol,1-acetate, (1S,3R)- Specification

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