5763-49-5

Basic information

• Product Name: tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione
• Synonyms: tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione;(3AS,6AR)-TETRAHYDRO-CYCLOPENTA[C]FURAN-1,3-DIONE;Tetrahydrocyclopenta[c]furan-1,3-dione;NSC 159314;Tetrahydro-1H-cyclopenta[c]furan-1,3(3aH);(3aR,6aS)-tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione
• CAS NO: 5763-49-5
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.13662
• EINECS: 227-286-1
• Mol File: 5763-49-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 289℃
• Flash Point: 140℃
• Appearance: /
• Density: 1.309
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione(5763-49-5)
• EPA Substance Registry System: tetrahydro-1H-cyclopenta[c]furan-1,3(3aH)-dione(5763-49-5)

Safety Data

• Hazardous Substances Data: 5763-49-5(Hazardous Substances Data)

Usage

Chemical Properties

brownish liquid

InChI:InChI=1/C7H8O3/c8-6-4-2-1-3-5(4)7(9)10-6/h4-5H,1-3H2

Synthetic route

cis-1,2-cyclopentanedicarboxylic acid (1461-96-7) → 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5)

Conditions	Yield
at 150 - 160℃; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid / 180 °C 2: acetyl chloride / 140 °C / im Einschlussrohr View Scheme
With acetic anhydride for 20h; Heating / reflux;

trans-1,2-cyclopentanedicarboxylic acid (80656-14-0) → 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5)

Conditions	Yield
at 300℃; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetic anhydride anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetyl chloride at 140℃; im Einschlussrohr; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);
With acetic anhydride anschliessend Erhitzen auf 170grad bei 20 mmHg Druck; anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);
Multi-step reaction with 2 steps 1: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern 2: 150 - 160 °C View Scheme

1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester (50708-47-9) → 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid; concentrated sulfuric acid; water 2: acetic acid anhydride / Loesen in Wasser oder in Kalilauge und Ansaeuern 3: 150 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: glacial acetic acid; concentrated sulfuric acid; water 2: acetic acid anhydride View Scheme

(trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4) → 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5)

Conditions	Yield
In benzene	8.60 g (81%)

methanol (67-56-1) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → (+/-)-cis-2-(methoxycarbonyl)cyclopentane carboxylic acid

Conditions	Yield
at 50 - 55℃; for 5h;	98%
at 50 - 55℃; for 16h;

carbon tetrabromide (558-13-4) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 3-(dibromomethylene)hexahydro-1H-cyclopenta[c]furan-1-one

Conditions	Yield
Stage #1: carbon tetrabromide With triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #3: 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	24%

(R)-Phenylglycinol (56613-80-0) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopentanecarboxylic acid (86331-36-4, 95462-66-1)

Conditions	Yield
In tetrahydrofuran 1.) 0 deg C, 15 min; 2.) r.t., 1 h;

methylamine (74-89-5) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → N-Methylcyclopentane-1,2-dicarboximide (71099-01-9)

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) + KOH-solution → cis-1,2-cyclopentanedicarboxylic acid (1461-96-7)

Conditions	Yield
durch Ansaeuern; anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2);

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) + air → trans-1,2-cyclopentanedicarboxylic acid (80656-14-0)

Conditions	Yield
anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → anhydride of/the/ cis-cyclopentane-dicarboxylic acid-(1.2)

Conditions	Yield
bei der Destillation unter vermindertem Druck; anhydride of/the/ trans-cyclopentane-dicarboxylic acid-(1.2);

thiazol-2-ylzinc(II) bromide (173382-28-0) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → trans-2-(1,3-thiazol-2-ylcarbonyl)cyclopentanecarboxylic acid

Conditions	Yield
Stage #1: thiazol-2-ylzinc(II) bromide; 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; Stage #2: With sodium hydroxide In tetrahydrofuran; diethyl ether; water Stage #3: With hydrogenchloride In water pH=1;

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → (1S,5R)-3-oxabicyclo[3.3.0]octan-2-one (75658-84-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C 3: 1 N HCl in MeOH / 2 h / Heating 4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C 5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C 6: 2 N H2SO4 / 2 h / 80 °C View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → (3aS,6aR)-hexahydro-1H-cyclopenta[c]furan-1-one (121960-86-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C 3: 1 N HCl in MeOH / 2 h / Heating 4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C 5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C 6: 2 N H2SO4 / 2 h / 80 °C View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 2-Hydroxymethyl-cyclopentanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide (86331-50-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C 3: 1 N HCl in MeOH / 2 h / Heating 4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C 5: 96 percent / NaBH4 / aq. ethanol / 4 h / 50 °C View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 2-((R)-2-Hydroxy-1-phenyl-ethyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione (86331-31-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C 3: 1 N HCl in MeOH / 2 h / Heating View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-hexahydro-cyclopenta[c]pyrrol-1-one (86331-45-5, 95462-61-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C 3: 1 N HCl in MeOH / 2 h / Heating 4: 94 percent / NaAlH2(OCH2CH2OCH3)2 / toluene / 4 h / -78 °C View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → Acetic acid (R)-2-(1,3-dioxo-hexahydro-cyclopenta[c]pyrrol-2-yl)-2-phenyl-ethyl ester (86338-97-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.) 0 deg C, 15 min; 2.) r.t., 1 h 2: sodium acetate / 3 h / 100 °C View Scheme

2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → N-methylcyclopentane-1,1-dicarboximide (71099-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 2: 51 percent / acetonitrile / 8 h / Irradiation View Scheme

benzylamine (100-46-9) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → N-benzyl-3-azabicyclo[3.3.0]octane-2,4-dione (111939-08-3)

Conditions	Yield
In tetrahydrofuran for 18h; Heating / reflux;

3,5-Dichloroaniline (626-43-7) + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → C13H13Cl2NO3 (1190849-68-3)

Conditions	Yield
In tetrahydrofuran at 55℃;

(S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine + 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione (5763-49-5) → 2-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione hydrochloride

Conditions	Yield
Stage #1: (S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-amine; 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux; Stage #2: With hydrogenchloride In water at 20℃;	0.33 g

Upstream product

• 1461-96-7 cis-1,2-cyclopentanedicarboxylic acid 
• 21917-20-4 (trans)-1,2-cyclopentanedicarboxylic acid 
• 50708-47-9 1,1,2,2-Cyclopentantetracarbonsaeure-tetraethylester 
• 80656-14-0 trans-1,2-cyclopentanedicarboxylic acid 

Downstream Products

• 111939-08-3 N-benzyl-3-azabicyclo[3.3.0]octane-2,4-dione 
• 40482-10-8 2-carbamoylcyclopentanecarboxylic acid 
• 86338-97-8 Acetic acid (R)-2-(1,3-dioxo-hexahydro-cyclopenta[c]pyrrol-2-yl)-2-phenyl-ethyl ester 
• 86331-45-5 3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-hexahydro-cyclopenta[c]pyrrol-1-one 
• 86331-31-9 2-((R)-2-Hydroxy-1-phenyl-ethyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione 
• 86331-50-2 2-Hydroxymethyl-cyclopentanecarboxylic acid ((R)-2-hydroxy-1-phenyl-ethyl)-amide 
• 1461-96-7 cis-1,2-cyclopentanedicarboxylic acid 

Relevant articles and documents

INHIBITORS OF DIACYLGLYCEROL O-ACYLTRANSFERASE TYPE 1 ENZYME

The present invention relates to compounds of formula (I) wherein R1, R3, X, Q, Z, A, D, m, and n are defined herein. Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.

Prostaglandin analogs

Thromboxane receptor antagonist activity is exhibited by compounds of the formula STR1 wherein: V is --(CH 2) m --, --O--, or STR2 but if V is --O--or STR3 R 3 and R 4 must complete an aromatic ring; W is --(CH 2) 2 --, --CH CH-- or phenylene;X is a single bond, --CH CH--, --(CH 2) n --, or --O--(CH 2) n --; or X is branched alkylene or --O--branched alkylene wherein W is linked to Y through a chain n carbon atoms long;Y is --CO 2 H, --CO 2 alkyl, --CO 2 alkali metal, --CH 2 OH, --CONHSO 2 R 5, --CONHR 6, or --CH 2 -5-tetrazolyl;Z is O or NH;R 3 and R 4 are each independently hydrogen or alkyl or R 3 and R 4 together complete a ring optionally substituted through a ring carbon with a halo, lower alkyl, phenyl, halo (lower alkyl), halophenyl, oxo or hydroxyl group; and the remaining symbols are as defined in the specification.