CID 12076969

Base Information

• Chemical Name: CID 12076969
• CAS No.: 31753-00-1
• Molecular Formula: C28H30 O5
• Molecular Weight: 446.543
• European Community (EC) Number: 608-668-0
• Nikkaji Number: J1.981.785G
• Mol file: 31753-00-1.mol

Synonyms:[(3As,4S,5S,6aR)-2-oxo-4-[(E)-3-oxooct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate;31753-00-1

Chemical Property of CID 12076969

Chemical Property:

• Vapor Pressure: 2.67E-16mmHg at 25°C
• Boiling Point: 640.5oC at 760 mmHg
• Flash Point: 273.6oC
• PSA: 69.67000
• Density: 1.20
• LogP: 5.53620
• Storage Temp.: 2-8°C
• Solubility.: DCM, Ethyl Acetate
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 446.20932405
• Heavy Atom Count: 33
• Complexity: 714

Purity/Quality:

99.9% ^*data from raw suppliers

(3aR,4R,5R,6aS)-Hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-ylEster[1,1’-Biphenyl]-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)C=CC1C(CC2C1CC(=O)O2)OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4
• Isomeric SMILES: CCCCCC(=O)/C=C/[C@@H]1[C@H](C[C@@H]2[C@H]1CC(=O)O2)OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4
• Uses: (3aR,4R,5R,6aS)-Hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl Ester [1,1’-Biphenyl]-4-carboxylic Acid is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.

Technology Process of CID 12076969

There total 17 articles about CID 12076969 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: 73.0%

dimethyl 2-oxoheptylphosphonate (36969-89-8) + (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (38754-71-1) → [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester (31753-00-1)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; stereoselective reaction;

DOI:10.1039/d1sc03237b

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester (31753-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sulfuric acid / 70 °C / 12751.3 Torr

2.1: sodium methylate / methanol / 25 °C

2.2: 25 °C

3.1: C₂₁H₂₁NOSi; copper dichloride; N-ethyl-N,N-diisopropylamine / acetonitrile; dichloromethane / 14 h / -20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; carbonic acid dimethyl ester; trichloroisocyanuric acid / ethyl acetate

5.1: sodium hydroxide / dichloromethane; water

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; sulfuric acid; sodium methylate; C₂₁H₂₁NOSi; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester; sodium hydroxide; copper dichloride; In methanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1039/d1sc03237b

Reference yield:

4-biphenyl-carboxylic acid chloride (14002-51-8) → [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester (31753-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C

3: NaH / 1,2-dimethoxy-ethane / 0 - 20 °C

With pyridine; dimethylsulfide; sodium hydride; ozone; In 1,2-dimethoxyethane;

DOI:10.1016/S0957-4166(00)80017-8

upstream raw materials:

Biphenyl-4-carboxylic acid (3aR,5R,6aS)-4-formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

dimethyl 2-oxoheptylphosphonate

4-biphenyl-carboxylic acid chloride

(3aR,6aS)-4-Vinyl-tetrahydro-cyclopenta[b]furan-2,5-dione

Downstream raw materials:

(1S,5R,6R,7R)-6-[(E)-3(S)-hydroxy-1-octenyl]-7-(4-phenyl-benzoyloxy)-2-oxabicyclo[3.3.0]octane-3-one

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-2-oxo-4-(3-oxo-octyl)-hexahydro-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E,3S)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E,3R)-3-hydroxy-3-methyl-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

Refernces

• 1、 -. "Treatment of inflammation with 15-keto-prostaglandin compounds". . . Retrieved 2008/06/13.
• 2、 -. "Treatment of pancreatic disease with 15-keto-prostaglandin compounds". . . Retrieved 2008/06/13.