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29783-26-4

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29783-26-4 Usage

Uses

cis-4-Cyclopentene-1,3-diol is an important building block for the synthesis of natural products with cyclopentanoid structure elements. It was used in preparation of key intermediates of prostaglandin synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 29783-26-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,7,8 and 3 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 29783-26:
(7*2)+(6*9)+(5*7)+(4*8)+(3*3)+(2*2)+(1*6)=154
154 % 10 = 4
So 29783-26-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c6-4-1-2-5(7)3-4/h1-2,4-7H,3H2/t4-,5+

29783-26-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name CIS-3,5-DIHYDROXY-1-CYCLOPENTENE

1.2 Other means of identification

Product number -
Other names cis-3,5-Dihydroxy-1-cyclopenten

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:29783-26-4 SDS

29783-26-4Synthetic route

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

cyclopenta-1,3-diene

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
54664-61-8

cis-1,4-diacetoxy-2-cyclopentene

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
6573-26-8

cyclopentadiene endoperoxide

A

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

cis-1α,2α,4α,6α-3,7-dioxatricyclo<4.1.0.02,4>heptane

B

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

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

A

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

cis-4-cyclopentene-1,3-diol

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

trans-3,5-dihydroxycyclopent-1-ene

Conditions
ConditionsYield
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
63603-17-8

(-)-2-cyclopenten-1(R),4(S)-diyl bis-N-mesyl-(S)-phenylalaninate

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
With barium dihydroxide In methanol; water for 4h; Ambient temperature;68%
maleic anhydride
930-60-9

maleic anhydride

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
With sodium tetrahydroborate; cerium(III) chloride In methanol58%
With methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate at 0℃; for 0.5h;
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
6573-26-8

cyclopentadiene endoperoxide

A

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
60410-16-4

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

1-Nitropropane
108-03-2

1-Nitropropane

A

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

cis-4-cyclopentene-1,3-diol

B

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

(+/-)-3-(1'-nitropropyl)cyclopentanone

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; regioselective reaction;A 20%
B 40%
cyclopentadiene endoperoxide
6573-26-8

cyclopentadiene endoperoxide

thiourea
17356-08-0

thiourea

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

cis-4-cyclopentene-1,3-diol

cyclopentadiene endoperoxide
6573-26-8

cyclopentadiene endoperoxide

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
With thiourea
With thiourea In dichloromethane; water
cis-3,5-dibromocyclopentene
17040-70-9

cis-3,5-dibromocyclopentene

tetraethylammonium acetate
1185-59-7

tetraethylammonium acetate

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
7129-41-1

6-oxabicyclo[3.1.0]hex-2-ene

A

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

cis-4-cyclopentene-1,3-diol

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

(+/-)-trans-cyclopentene-(1)-diol-(3.4)

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

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

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

trans-3,5-dihydroxycyclopent-1-ene

Conditions
ConditionsYield
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
542-92-7

cyclopenta-1,3-diene

A

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

cis-4-cyclopentene-1,3-diol

B

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

cis/trans-Cyclopent-3-en-1,2-diol

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

trans-3,5-dihydroxycyclopent-1-ene

Conditions
ConditionsYield
With peracetic acid; sodium acetate; sodium carbonate In dichloromethane; water; acetic acid for 1h; Ambient temperature;
cis-4-(trityloxy)cyclopent-2-enol

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

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 55℃; for 8h;58 mg
cis-3-acetoxy-5-hydroxycyclopent-1-ene
61740-26-9

cis-3-acetoxy-5-hydroxycyclopent-1-ene

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

tert-butyl alcohol
75-65-0

tert-butyl alcohol

1 mol H2O2

1 mol H2O2

OsO4

OsO4

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
at 0℃;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

(AsCF3)4.5

(AsCF3)4.5

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
98-00-0

(2-furyl)methyl alcohol

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
61305-35-9, 61305-36-0, 61740-33-8, 56745-67-6

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
183612-95-5

4-trityloxy-2-cyclopentenone

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
542-92-7

cyclopenta-1,3-diene

hydroxylamine hydrochloride

hydroxylamine hydrochloride

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
6573-26-8

2,3-dioxabicyclo[2.2.1]hept-5-ene

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
54664-61-8

cis-1,4-diacetoxy-2-cyclopentene

A

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

cis-4-cyclopentene-1,3-diol

B

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

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

C

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

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

Conditions
ConditionsYield
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)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

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

cis-4-cyclopentene-1,3-diol

Conditions
ConditionsYield
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
108-05-4

vinyl acetate

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

cis-4-cyclopentene-1,3-diol

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

cis-1,4-diacetoxy-2-cyclopentene

Conditions
ConditionsYield
With lipase from candida antartica; triethylamine In tetrahydrofuran at 20℃; for 0.5h; Enzymatic reaction; enantioselective reaction;100%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

acetic anhydride
108-24-7

acetic anhydride

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

cis-1,4-diacetoxy-2-cyclopentene

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

Tosyl isocyanate
4083-64-1

Tosyl isocyanate

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

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

Conditions
ConditionsYield
C36H84O12P4Pd In tetrahydrofuran Heating;97%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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%
aqueous NaCl

aqueous NaCl

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

cis-4-cyclopentene-1,3-diol

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

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

cis-1,4-diacetoxy-2-cyclopentene

Conditions
ConditionsYield
With pyridine; hydrogenchloride; acetic anhydride In dichloromethane96.4%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

A

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

(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)

B

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

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

cis-cyclopentane-1,3-diol

Conditions
ConditionsYield
With potassium diazodicarboxylate; acetic acid In methanol at 0℃; Inert atmosphere;94%
With hydrogen; platinum(IV) oxide
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

4-hydroxybenzenediazonium tetrafluoroborate

4-hydroxybenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

butyryl chloride
141-75-3

butyryl chloride

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

cis-Cyclopent-2-ene-1,4-diyl dibutanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 3h; Ambient temperature;92%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

benzoyl chloride
98-88-4

benzoyl chloride

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

cis 2-cyclopentene 1,4-dibenzoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;92%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

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

cis-1,4-Bis(t-Butyldimethylsilyl)cyclopent-2-ene-1,4-diol

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

acetic anhydride
108-24-7

acetic anhydride

A

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

cis-1,4-diacetoxy-2-cyclopentene

B

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

isobutyryl chloride
79-30-1

isobutyryl chloride

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

(1R,3S)-cyclopent-4-ene-1,3-diyl bis(isobutyrate)

Conditions
ConditionsYield
With triethylamine In dichloromethane for 3h; Ambient temperature;87%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

bromoacetic acid
79-08-3

bromoacetic acid

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

((1S,4R)-4-Carboxymethoxy-cyclopent-2-enyloxy)-acetic acid

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 60℃;86%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

2-methoxyphenyldiazonium tetrafluoroborate
492-95-5

2-methoxyphenyldiazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

2-hydroxybenzenediazonium tetrafluoroborate

2-hydroxybenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

propionyl chloride
79-03-8

propionyl chloride

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

cis-Cyclopent-2-ene-1,4-diyl dipropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 3h; Ambient temperature;84%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

isopropyl chloroformate
108-23-6

isopropyl chloroformate

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

meso-cyclopent-4-ene-1,3-diyl diisopropyl dicarbonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃;84%
cis-4-cyclopentene-1,3-diol
29783-26-4

cis-4-cyclopentene-1,3-diol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

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

cyclopent-4-ene-1,3-diyl diethyl dicarbonate

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

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

di-tert-butylsilyl bis(trifluoromethanesulfonate)

cis-3,5-cyclopent-1-ene

cis-3,5-cyclopent-1-ene

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane 0 deg C, 10 min; without cooling, 30 min;80%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

cis-4-cyclopentene-1,3-diol

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

carbonic acid 4-tert-butoxycarbonyloxy-cyclopent-2-enyl ester tert-butyl ester

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
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
108-05-4

vinyl acetate

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

cis-4-cyclopentene-1,3-diol

A

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

cis-1,4-diacetoxy-2-cyclopentene

B

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

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

Conditions
ConditionsYield
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
29783-26-4

cis-4-cyclopentene-1,3-diol

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

(R)-(+)-4-hydroxy-2-cyclopentenone

Conditions
ConditionsYield
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

29783-26-4Relevant articles and documents

Structure-activity relationships of untenone a and its derivatives for inhibition of DNA polymerases

Saito, Fumiyo,Takeuchi, Ryo,Kamino, Tomoyuki,Kuramochi, Kouji,Sugawara, Fumio,Sakaguchi, Kengo,Kobayashi, Susumu

, p. 1975 - 1977 (2004)

We found that untenone A and mannzamenone A inhibit mammalian DNA polymerases α and β, and human terminal deoxynucleotidyl transferase (TdT). The syntheses of both compounds and the structure-activity relationships of untenone A derivatives are described.

Molecular Design of Crown Ethers. 6. Substitution Effect in 16-Crown-5

Inoue, Yoshihisa,Wada, Kazuhito,Liu, Yu,Ouchi, Mikio,Tai, Akira,Hakushi, Tadao

, p. 5268 - 5272 (1989)

A number of 14-, 15-, and/or 16-substituted 16-crown-5 derivatives were synthesized for systematic analysis of the effect of substitution in these crown ethers.The cation-binding ability of substituted 16-crown-5 rings was evaluated by the solvent extraction technique and found to be a critical function of the position, number, type, and stereochemistry of the substituent(s) introduced.Both 15- and 14/16-substituted 16-crown-5 exhibited gradually decreased extractabilities with increasing substitution, although the profiles of change in extractability were distinctly different between 15- and 14/16-substitution.The substitution-induced decrease of extractability is attributed to the limited access of counteranion and/or to the lack of conformational adjustments necessary to make a structure suitable for complex formation.The bridging substitutions at 14- and 16-positions dramatically enhanced the extractabilities for all cations without lowering the original relative cation selectivity.This may arise from the favorable entropic contribution of the conformational freezing by bridging substitution.

-

Blomquist,Mayes

, p. 134,139 (1945)

-

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts

Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.

supporting information, p. 10102 - 10112 (2021/08/03)

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

A Pd-catalyzed asymmetric allylic substitution cascade: Via an asymmetric desymmetrization for the synthesis of bicyclic dihydrofurans

Xu, Kai,Liu, Hao,Hou, Yilin,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin

supporting information, p. 13295 - 13298 (2019/11/13)

A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with the desired products being obtained in high yields and with up to 97% ee. The reaction was performed on a gram-scale and the corresponding bicyclic dihydrofurans could undergo several transformations. The methodology provides an efficient synthetic route to biologically active chiral bicyclic dihydrofurans derivatives.

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