Dinoprost

Base Information

• Chemical Name: Dinoprost
• CAS No.: 23518-25-4
• Deprecated CAS: 13535-33-6,99437-94-2
• Molecular Formula: C20H34 O5
• Molecular Weight: 354.487
• European Community (EC) Number: 684-259-0
• UNII: B7IN85G1HY
• DSSTox Substance ID: DTXSID9022946
• Nikkaji Number: J9.246K
• Wikipedia: Prostaglandin_F2alpha,Dinoprost
• Wikidata: Q421375
• NCI Thesaurus Code: C65413
• Pharos Ligand ID: GCAJ7BC694FA
• Metabolomics Workbench ID: 2372
• ChEMBL ID: CHEMBL815
• Mol file: 23518-25-4.mol

Synonyms:9alpha,11beta PGF2;9alpha,11beta-PGF2;alpha, PGF2;Dinoprost;Enzaprost F;Estrofan;F2 alpha, Prostaglandin;F2alpha, Prostaglandin;PGF2;PGF2 alpha;PGF2alpha;Prostaglandin F2;Prostaglandin F2 alpha;Prostaglandin F2alpha

Chemical Property of Dinoprost

Chemical Property:

• Vapor Pressure: 1.71E-13mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 531°Cat760mmHg
• Flash Point: 289°C
• PSA: 97.99000
• Density: 1.153g/cm³
• LogP: 3.04290
• Storage Temp.: -20°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

99%, ^*data from raw suppliers

(+-)-PGF2-ALPHA 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 20-35
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
• 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
• Recent ClinicalTrials: In Vitro Myometrial Contractions in Laboring and Non-laboring Women

Technology Process of Dinoprost

There total 73 articles about Dinoprost which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

C15H26O4 + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1038/nature11411

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + (1α,5α)-3β-hydroxy-2α-<(E)-(3S*)-3-hydroxyoct-1-enyl>bicyclo<3.2.0>heptan-6-one (67728-76-1,73089-05-1,74843-57-5,78037-95-3,108692-60-0,108692-61-1,114420-80-3) → (+/-)-prostaglandin-F2α (23518-25-4) + 2β-<(E)-3-hydroxyoct-1-enyl>cyclopent-3-en-1α-ol (82978-04-9) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) acetonitrile, H₂O, irradiation, 4.5 h, 2.) THF, 1 h;

Reference yield:

(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran

2.1: ozone / methanol; dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(Z)-7-{(1S,2S,3S,5R)-2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-3-methoxymethoxy-cyclopentyl}-hept-5-enoic acid

trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone

trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene

Refernces

• 1、 Mahrwald, Rainer,Schick, Hans,Pivnitsky, Kasimir K.,Schwarz, Sigfrid. "Prostaglandins and Prostaglandin Intermediates. Part 26 A Novel Route to PGF2α using Triisopropoxy-hept-1-ynyl-titanium as Precursor for the β-Side Chain". . p. 403 - 413. Retrieved 2007/10/02.
• 2、 Marino, Joseph P.,Pradilla, Roberto F. de la,Laborde, Edgardo. "Regio- and Stereoselectivity of the Reaction between Cyanocuprates and Cyclopentene Epoxides. Application to the Total Synthesis of Prostaglandins". . p. 4898 - 4913. Retrieved 2007/10/02.