dinoprost
Conditions | Yield |
---|---|
With hydrogenchloride In water; acetone at 20℃; for 0.333333h; Inert atmosphere; | 99% |
methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate
dinoprost
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol Ambient temperature; | 95% |
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; |
(+)-prostaglandin F2α
dinoprost
Conditions | Yield |
---|---|
With water In tert-butyl methyl ether at 35℃; for 18h; Enzymatic reaction; | 90% |
base hydrolysis; Yield given; |
(Z)-7-((1R,2R,3R,5S)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(S,E)-3-[(tert-butyldimethylsilanyl)oxy]oct-1-en-1-yl}-5-hydroxycyclopentyl)hept-5-enoic acid
dinoprost
Conditions | Yield |
---|---|
With hydrogen fluoride; water In acetonitrile at 20℃; for 7h; stereoselective reaction; | 90% |
With hydrogenchloride In tetrahydrofuran; water at -78 - 20℃; for 6h; | 89% |
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 6h; Inert atmosphere; | 89% |
(Z)-7-[(1R,2R,3R,5S)-3-Benzyloxy-2-((E)-(S)-3-benzyloxy-oct-1-enyl)-5-hydroxy-cyclopentyl]-hept-5-enoic acid
dinoprost
Conditions | Yield |
---|---|
With ammonia; sodium | 75% |
Conditions | Yield |
---|---|
With (Z)-2-Butene; C37H40Cl2N2ORuS2 In tetrahydrofuran at 22℃; under 7 Torr; Pressure; Inert atmosphere; Glovebox; Sealed tube; | 75% |
(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
(4-carboxybutyl)triphenylphosphonium bromide
dinoprost
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; Wittig Olefination; | 55% |
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Wittig Olefination; Schlenk technique; Inert atmosphere; Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Schlenk technique; Inert atmosphere; | 152 mg |
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; | 152 mg |
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Wittig Olefination; Schlenk technique; Inert atmosphere; Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1.5h; Wittig Olefination; Schlenk technique; Inert atmosphere; | 24.8 mg |
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 70 mg |
(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
(4-carboxybutylene)triphenylphosphorane
dinoprost
Conditions | Yield |
---|---|
Stage #1: (4-carboxybutylene)triphenylphosphorane With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 0.666667h; Inert atmosphere; Stage #2: (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol In tetrahydrofuran at 20℃; for 1h; | 54% |
(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
4-carboxybutyliden triphenylphosphorane sodium
dinoprost
Conditions | Yield |
---|---|
53% |
Conditions | Yield |
---|---|
In water for 0.166667h; Gersemia fruticosa preparation, pH 8.5; | A 20% B 20% C 20% |
Conditions | Yield |
---|---|
With ammonia; lithium In tetrahydrofuran Product distribution; | A 8 % Chromat. B 92 % Chromat. |
(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
5-(Triphenyl-λ5-phosphanylidene)-pentanoic acid anion
dinoprost
Conditions | Yield |
---|---|
Yield given; |
(3aR,4R,5R,6aS)-5-Trimethylsilanyloxy-4-((E)-(S)-3-trimethylsilanyloxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-ol
dinoprost
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
4-carboxybutyliden triphenylphosphorane sodium
(3aR,4R,5R,6aS)-4-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
dinoprost
Conditions | Yield |
---|---|
With acetic acid Yield given. Multistep reaction; |
methyl 11α-acetoxy-9α,15(S)-dihydroxy-5-cis-13-transprostadienoate
dinoprost
dinoprost
Conditions | Yield |
---|---|
With water; hydrogen cation Yield given; |
15-(t-butyldiphenylsilyl) PGF2α
dinoprost
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 48h; Yield given; |
dinoprost
Conditions | Yield |
---|---|
With tin(ll) chloride |
all cis 5,8,11,14-eicosatetraenoic acid
A
prostaglandin D2
B
dinoprostone
C
dinoprost
Conditions | Yield |
---|---|
With Tris HCl buffer; GLUTATHIONE; prostaglandin synthetase; L-epinephrine at 37℃; for 0.0833333h; Product distribution; var. prostaglandin synthetase source (animal and tissue); var. conc. of reactants; var. time; |
all cis 5,8,11,14-eicosatetraenoic acid
A
prostaglandin D2
B
dinoprostone
C
dinoprost
Conditions | Yield |
---|---|
With HUV-EC-C at 37℃; for 0.166667h; Enzyme kinetics; Further Variations:; Reagents; Cyclization; Enzymatic reaction; |
dinoprost
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran for 48h; |
dinoprost
Conditions | Yield |
---|---|
With hydrogenchloride |
Prostaglandin G2
dinoprost
Conditions | Yield |
---|---|
With 4-methylaminoantirypine |
(-)-7α-hydroxy-6β-(3α-hydroxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one
dinoprost
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / pyridine / 3 h / Ambient temperature 2: 0.27 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -70 - -65 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 - 5 °C / Inert atmosphere 2.2: 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere View Scheme |
(-)-7α-trimethylsilyloxy-6β-(3α-trimethylsilyloxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one
dinoprost
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.27 g / i-Bu2AlH / CH2Cl2 / 1 h / -78 °C View Scheme |
(S)-tert-butyl-dimethyl(oct-1-en-3-yloxy)silane
dinoprost
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: second generation Grubb's catalyst / CH2Cl2 / 12 h / 40 °C 2: DIBAL-H / -78 °C 3: HCl View Scheme | |
Multi-step reaction with 3 steps 1.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 12 h / Inert atmosphere; Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: hydrogenchloride / water; acetone / 0.33 h / 20 °C / Inert atmosphere View Scheme |
(3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-vinylhexahydro-2H-cyclopenta[b]furan-2-one
dinoprost
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: second generation Grubb's catalyst / CH2Cl2 / 12 h / 40 °C 2: DIBAL-H / -78 °C 3: HCl View Scheme | |
Multi-step reaction with 4 steps 1: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 2: DIBAL-H / CH2Cl2 / -78 °C 3: KOtBu / tetrahydrofuran 4: HCl / tetrahydrofuran / 48 h View Scheme |
The Prostaglandin F2α, with the CAS registry number 551-11-1, is also known as l-Prostaglandin F2-alpha. It belongs to the product category of Prostaglandins. This chemical's molecular formula is C20H34O5 and molecular weight is 354.48096. Its IUPAC name is called (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid. This chemical's classification codes are Abortifacient Agents; Abortifacient agents, nonsteroidal; Drug / Therapeutic Agent; Hormone; Human Data; Mutation data; Oxytocic; Oxytocics; Prostaglandin; Reproductive Control Agents; Reproductive Effect.
Physical properties of Prostaglandin F2α: (1)ACD/LogP: 2.14; (2)ACD/LogD (pH 5.5): 1.33; (3)ACD/LogD (pH 7.4): -0.47; (4)ACD/BCF (pH 5.5): 3.86; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 53.76; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 15; (11)Index of Refraction: 1.569; (12)Molar Refractivity: 100.75 cm3; (13)Molar Volume: 307.3 cm3; (14)Surface Tension: 48.6 dyne/cm; (15)Density: 1.153 g/cm3; (16)Flash Point: 289 °C; (17)Enthalpy of Vaporization: 92.76 kJ/mol; (18)Boiling Point: 531 °C at 760 mmHg; (19)Vapour Pressure: 1.71E-13 mmHg at 25°C.
Preparation: In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular phase.
Uses of Prostaglandin F2α: Prostaglandin F2α is pharmaceutically termed Dinoprost is a naturally-occurring prostaglandin used in medicine to induce labor and as an abortifacient.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
(2)Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
(3)InChI: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
(4)InChIKey: PXGPLTODNUVGFL-YNNPMVKQSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intramuscular | 152mg/kg (152mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
mouse | LD50 | oral | 1300mg/kg (1300mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
mouse | LD50 | subcutaneous | 212mg/kg (212mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
rabbit | LD50 | intramuscular | > 10mg/kg (10mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 261, 1978. |
rabbit | LD50 | intravenous | 2500ug/kg (2.5mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 261, 1978. |
rat | LD50 | intramuscular | 112mg/kg (112mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
rat | LD50 | intravenous | 106mg/kg (106mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
rat | LD50 | oral | 1170mg/kg (1170mg/kg) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 2, Pg. 403, 1971. |
rat | LD50 | subcutaneous | 95mg/kg (95mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 4, Pg. 193, 1973. | |
women | TDLo | intravenous | 20ug/kg (0.02mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Japan Medical Gazette. Vol. 10(7), Pg. 9, 1973. |
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