ENONE-L

Base Information

• Chemical Name: ENONE-L
• CAS No.: 933789-26-5
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.354
• Mol file: 933789-26-5.mol

Synonyms:ENONE-L;(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property of ENONE-L

Chemical Property:

• Vapor Pressure: 4.65E-11mmHg at 25°C
• Boiling Point: 506°C at 760 mmHg
• Flash Point: 185.3°C
• Density: 1.282g/cm³

Purity/Quality:

98% ^*data from raw suppliers

Enone-L for latanoprost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ENONE-L

There total 8 articles about ENONE-L 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: 88.0%

dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0) + Corey aldehyde (62961-72-2) → (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (933789-26-5)

Guidance literature:

dimethyl(2-oxo-4-phenylbutyl)phosphonate; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

Corey aldehyde; In tetrahydrofuran; at 20 ℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (933789-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: formic acid; sulfuric acid / 24 h / 80 °C

1.2: 2 h / 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

With formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sulfuric acid; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1002/anie.201902371

Reference yield:

C24H34O4Si → C18H20O4 (933789-26-5)

Guidance literature:

With hydrogenchloride; In water; acetone; for 0.5h; pH=2;

upstream raw materials:

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

cyclopenta-1,3-diene

Refernces

• 1、 Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er. "Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation". . p. 9923 - 9927. Retrieved 2019/05/16.
• 2、 -. "PROCESS FOR THE PRODUCTION OF INTERMEDIATES FOR MAKING PROSTAGLANDIN DERIVATIVES SUCH AS LATANOPROST, TRAVAPROST, AND BIMATOPROST". Page/Page column 7-8. . Retrieved 2008/06/13.