(Z)-7-[(1R,2R)-2-[(E)-oct-2-enyl]-5-oxocyclopentyl]hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2R)-2-[(E)-oct-2-enyl]-5-oxocyclopentyl]hept-5-enoic acid
• CAS No.: 142666-04-4
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.472
• Mol file: 142666-04-4.mol

Synonyms:(+)(-)-8,12-trans-9-oxo-prosta-5,14-dienoic acid;8,12-OPA;8,12-trans-(5Z-14Z)-9-oxo-prosta-5,14-dienoic acid

Chemical Property of (Z)-7-[(1R,2R)-2-[(E)-oct-2-enyl]-5-oxocyclopentyl]hept-5-enoic acid

Chemical Property:

• Vapor Pressure: 5.98E-10mmHg at 25°C
• Boiling Point: 465.4°Cat760mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 249.4°C
• PSA: 54.37000
• Density: 0.989g/cm³
• LogP: 5.30950
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 409

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC1CCC(=O)C1CC=CCCCC(=O)O
• Isomeric SMILES: CCCCC/C=C/C[C@H]1CCC(=O)[C@@H]1C/C=C\CCCC(=O)O

Technology Process of (Z)-7-[(1R,2R)-2-[(E)-oct-2-enyl]-5-oxocyclopentyl]hept-5-enoic acid

There total 19 articles about (Z)-7-[(1R,2R)-2-[(E)-oct-2-enyl]-5-oxocyclopentyl]hept-5-enoic acid 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: 87.0%

(Z)-7-[(1S,2S)-2-((Z)-Oct-2-enyl)-5-oxo-cyclopentyl]-hept-5-enal (142666-05-5) → 8,12-trans-(5Z,14Z)-9-oxo-prosta-5,14-dienoic acid (142666-04-4,147804-40-8)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at -20 ℃;

Reference yield:

2-(4-pentyneyl)-1,3-dioxolane (98558-32-8) → 8,12-trans-(5Z,14Z)-9-oxo-prosta-5,14-dienoic acid (142666-04-4,147804-40-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) BuLi / 1.) THF, hexane, -40 deg C, 15 min, 2.) THF, hexane, -15 deg C, 1 h

2: 80 percent / PPh₃, CCl₄ / 1 h / Heating

3: 2.7 g / potassium carbonate / acetone / 8 h / Heating

4: 68 percent / palladium acetate / acetonitrile / 0.5 h / Heating

5: 97 percent / H₂, pyridine / 10percent Pd/C / ethyl acetate / Ambient temperature

6: 82 percent / NaOMe / methanol / 4 h / 0 °C

7: 78.6 percent / NaCl / dimethylsulfoxide; H₂O / 2 h / 175 °C

8: 74 percent / triethyl orthoformate, p-TsOH / 2 h / Heating

9: diisobutylaluminium hydride / tetrahydrofuran / 2 h / Ambient temperature

10: 1.) bis(trimethylsilyl)amide / 1.) HMPA, THF, 2 h, 2.) HMPA, THF, 12 h

11: 100 percent / aq. acetic acid / tetrahydrofuran / 4 h / 65 °C

12: 87 percent / CrO₃, conc. H₂SO₄ / -20 °C

With pyridine; chromium(VI) oxide; tetrachloromethane; n-butyllithium; sulfuric acid; hydrogen; hexamethyldisilazide; sodium methylate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; orthoformic acid triethyl ester; triphenylphosphine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; ethyl acetate; acetone; acetonitrile;

Reference yield:

2-(6-hydroxy-4-hexynyl)-1,3-dioxolane (110452-43-2) → 8,12-trans-(5Z,14Z)-9-oxo-prosta-5,14-dienoic acid (142666-04-4,147804-40-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / PPh₃, CCl₄ / 1 h / Heating

2: 2.7 g / potassium carbonate / acetone / 8 h / Heating

3: 68 percent / palladium acetate / acetonitrile / 0.5 h / Heating

4: 97 percent / H₂, pyridine / 10percent Pd/C / ethyl acetate / Ambient temperature

5: 82 percent / NaOMe / methanol / 4 h / 0 °C

6: 78.6 percent / NaCl / dimethylsulfoxide; H₂O / 2 h / 175 °C

7: 74 percent / triethyl orthoformate, p-TsOH / 2 h / Heating

8: diisobutylaluminium hydride / tetrahydrofuran / 2 h / Ambient temperature

9: 1.) bis(trimethylsilyl)amide / 1.) HMPA, THF, 2 h, 2.) HMPA, THF, 12 h

10: 100 percent / aq. acetic acid / tetrahydrofuran / 4 h / 65 °C

11: 87 percent / CrO₃, conc. H₂SO₄ / -20 °C

With pyridine; chromium(VI) oxide; tetrachloromethane; sulfuric acid; hydrogen; hexamethyldisilazide; sodium methylate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; orthoformic acid triethyl ester; triphenylphosphine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; ethyl acetate; acetone; acetonitrile;

upstream raw materials:

(Z)-7-[(1S,2S)-2-((Z)-Oct-2-enyl)-5-oxo-cyclopentyl]-hept-5-enal

2-(4-pentyneyl)-1,3-dioxolane

2-(6-hydroxy-4-hexynyl)-1,3-dioxolane

trans-2-<6-(1,3-dioxolan-2-yl)-Z-2-hexenyl>-3-(methylformyl)-cyclopentan-1-one ethyleneketal

Refernces

• 1、 Di Giacomo,Leggeri,Papeo,Pirillo,Traverso. "Synthesis of a 11-deoxyprostanoid in the area of Preclavulones: (±)- 8,12-trans-(5Z-14Z)-9-oxo-prosta-5,14-dienoic acid from 2-allyl-2- cyclopenten-1-one". . p. 379 - 385. Retrieved 2007/10/02.