11-Oxoprosta-5,12,14-trien-1-oic acid

Base Information

• Chemical Name: 11-Oxoprosta-5,12,14-trien-1-oic acid
• CAS No.: 596104-94-8
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• DSSTox Substance ID: DTXSID10693982
• Mol file: 596104-94-8.mol

Synonyms:DTXSID10693982;11-Oxoprosta-5,12,14-trien-1-oic acid

Chemical Property of 11-Oxoprosta-5,12,14-trien-1-oic acid

Chemical Property:

• PSA: 54.37000
• LogP: 5.22960
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

CAY10410 ≥98% (isomer mixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=C1C(CCC1=O)CC=CCCCC(=O)O

Technology Process of 11-Oxoprosta-5,12,14-trien-1-oic acid

There total 19 articles about 11-Oxoprosta-5,12,14-trien-1-oic 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: 39.0%

(Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enal → (Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid (596104-94-8)

Guidance literature:

With sodium chlorite; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 1.5h;

DOI:10.1021/acs.orglett.5b02181

Reference yield:

(Z)-ethyl 9-((4-methoxybenzyl)oxy)non-4-enoate → (Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid (596104-94-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere

2.1: lithium perchlorate; N-ethyl-N,N-diisopropylamine / dichloromethane; diethyl ether / 16 h / -78 °C / Inert atmosphere

3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 22 h / -78 °C / Inert atmosphere

4.1: triethylamine; 4-acetamidobenzenesulfonyl azide / acetonitrile / 10 h / 20 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

6.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / dichloromethane / 0.75 h / Inert atmosphere; Reflux

6.2: 16 h / 60 °C

7.1: sodium chloride / dimethyl sulfoxide / 0.92 h / 140 °C / Inert atmosphere

8.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

8.2: 3 h / -78 °C / Inert atmosphere

8.3: 1.5 h / -20 °C / Inert atmosphere

9.1: Stryker's reagent / water; benzene / 1.5 h

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C

11.1: pyridine; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

12.1: 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 20 °C

With pyridine; 1H-imidazole; sodium chlorite; n-butyllithium; 2-methyl-but-2-ene; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; 4-acetamidobenzenesulfonyl azide; Stryker's reagent; lithium perchlorate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: |Krapcho Dealkoxycarbonylation / 8.1: |Aldol Condensation / 8.2: |Aldol Condensation / 11.1: |Dess-Martin Oxidation;

DOI:10.1021/acs.orglett.5b02181

Reference yield:

(Z)-9-((4-methoxybenzyl)oxy)non-4-enal → (Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid (596104-94-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium perchlorate; N-ethyl-N,N-diisopropylamine / dichloromethane; diethyl ether / 16 h / -78 °C / Inert atmosphere

2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 22 h / -78 °C / Inert atmosphere

3.1: triethylamine; 4-acetamidobenzenesulfonyl azide / acetonitrile / 10 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

5.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / dichloromethane / 0.75 h / Inert atmosphere; Reflux

5.2: 16 h / 60 °C

6.1: sodium chloride / dimethyl sulfoxide / 0.92 h / 140 °C / Inert atmosphere

7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

7.2: 3 h / -78 °C / Inert atmosphere

7.3: 1.5 h / -20 °C / Inert atmosphere

8.1: Stryker's reagent / water; benzene / 1.5 h

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C

10.1: pyridine; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

11.1: 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 20 °C

With pyridine; 1H-imidazole; sodium chlorite; n-butyllithium; 2-methyl-but-2-ene; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; 4-acetamidobenzenesulfonyl azide; Stryker's reagent; lithium perchlorate; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 6.1: |Krapcho Dealkoxycarbonylation / 7.1: |Aldol Condensation / 7.2: |Aldol Condensation / 10.1: |Dess-Martin Oxidation;

DOI:10.1021/acs.orglett.5b02181

upstream raw materials:

1 ,5-pentanediol

(4R)-4-{(2Z)-7-[(4-methoxybenzyl)oxy]hept-2-en-1-yl}cyclopent-2-en-1-one

(S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone

5-(4-methoxybenzyloxy)-1-pentanol

Refernces

• 1、 Egger, Julian,Fischer, Stefan,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.. "Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12". . p. 4340 - 4343. Retrieved 2015/09/15.