13,14-Dihydro-15-keto-pgf2alpha

Base Information

• Chemical Name: 13,14-Dihydro-15-keto-pgf2alpha
• CAS No.: 27376-76-7
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• European Community (EC) Number: 631-095-2
• DSSTox Substance ID: DTXSID701019118
• Nikkaji Number: J39.477G
• Wikidata: Q27070766
• Pharos Ligand ID: GC3D1X9FPTN6
• Metabolomics Workbench ID: 2394
• Mol file: 27376-76-7.mol

Synonyms:13,14-dihydro-15-keto-PGF2alpha;13,14-dihydro-15-ketoprostaglandin F;13,14-dihydro-15-ketoprostaglandin F2alpha;13,14-dihydro-15-oxoprostaglandin F;15-K-DH-PGF(2alpha);15-keto-13,14-dihydro-PGF2alpha;15-keto-13,14-dihydro-prostaglandin F2alpha;15-keto-13,14-dihydroprostaglandin F2alpha;15-keto-dihydro-PGF2alpha;DHK-PGF2alpha;PGFM;pulmonary metabolite-PGF2alpha

Chemical Property of 13,14-Dihydro-15-keto-pgf2alpha

Chemical Property:

• Vapor Pressure: 4.72E-14mmHg at 25°C
• Boiling Point: 543°Cat760mmHg
• Flash Point: 296.2°C
• PSA: 94.83000
• Density: 1.091g/cm³
• LogP: 3.47510
• Storage Temp.: −20°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

99%,98%, ^*data from raw suppliers

13,14-dihydro-15-keto Prostaglandin F2α ≥95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)CCC1C(CC(C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
• Uses: 13,14-Dihydro-15-ketoPGF2α is a metabolite of PGF2α that binds bovine acetylcholine esterase.

Technology Process of 13,14-Dihydro-15-keto-pgf2alpha

There total 6 articles about 13,14-Dihydro-15-keto-pgf2alpha 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: 59.0%

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + 1-((3aR,5R,6aS)-2,5-Dihydroxy-hexahydro-cyclopenta[b]furan-4-yl)-octan-3-one (125010-78-8) → 15-oxo-13,14-dihydro-prostaglandin F2α (27376-76-7,67837-85-8,107615-77-0,191919-02-5)

Guidance literature:

With t-BuPK; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

1,2-epoxyheptane (5063-65-0) → 15-oxo-13,14-dihydro-prostaglandin F2α (27376-76-7,67837-85-8,107615-77-0,191919-02-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / n-BuLi, BF₃*Et₂O

2: 85 percent / Na₂HPO₄, sodium amalgam / methanol / 1.5 h / -30 °C

3: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, o.5 h, 2.) 15 min

4: 91 percent / aq. HCl / acetonitrile / 1 h / Ambient temperature

5: 59 percent / t-BuPK / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; oxalyl dichloride; t-BuPK; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; acetonitrile;

Reference yield:

4β-(3ξ-hydroxy-octan-1-yl)-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopenta/b/furan (125010-76-6) → 15-oxo-13,14-dihydro-prostaglandin F2α (27376-76-7,67837-85-8,107615-77-0,191919-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, o.5 h, 2.) 15 min

2: 91 percent / aq. HCl / acetonitrile / 1 h / Ambient temperature

3: 59 percent / t-BuPK / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; oxalyl dichloride; t-BuPK; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; acetonitrile;

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

1-((3aR,5R,6aS)-2,5-Dihydroxy-hexahydro-cyclopenta[b]furan-4-yl)-octan-3-one

1,2-epoxyheptane

4β-(3ξ-hydroxy-octan-1-yl)-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopenta/b/furan

Refernces