Enisoprost

Base Information

• Chemical Name: Enisoprost
• CAS No.: 81026-63-3
• Molecular Formula: C22H36 O5
• Molecular Weight: 380.52
• UNII: J85F4K48Q1
• DSSTox Substance ID: DTXSID201021627
• Wikidata: Q27281331
• NCI Thesaurus Code: C169950
• ChEMBL ID: CHEMBL266979
• Mol file: 81026-63-3.mol

Synonyms:11,16-dihydroxy-16-methyl-9-oxoprost-4,13-dien-1-oic acid;enisoprost

Chemical Property of Enisoprost

Chemical Property:

• Vapor Pressure: 1.15E-11mmHg at 25°C
• Boiling Point: 490.2°C at 760 mmHg
• PKA: 13.90±0.60(Predicted)
• Flash Point: 158.2°C
• PSA: 83.83000
• Density: 1.092g/cm³
• LogP: 3.72960
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 380.25627424
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

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

Enisoprost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)(CC=CC1C(CC(=O)C1CCC=CCCC(=O)OC)O)O
• Isomeric SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CC/C=C\CCC(=O)OC)O)O
• Uses: Enisoprost is the antisecretory prostaglandin derivative. Analogue of Prostaglandin E1 (P838600), which is the primary prostaglandin that is easily crystallized from purified biological extracts.

Technology Process of Enisoprost

There total 13 articles about Enisoprost 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:

(+/-)-methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-4-(Z)-heptenoate (78908-10-8) → Enisoprost (81026-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 1 h / Ambient temperature

2: 1.) n-BuLi, 2.) copper 1-pentyne, HMPT

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; copper 1-pentyne; In N,N-dimethyl-formamide;

DOI:10.1021/jm00360a002

Reference yield:

4R(+)-hydroxy-2-(6-methoxycarbonyl-3-cis-hexenyl)-2-cyclopentenone (85168-49-6) → (E)-7-[(1S,2S,3S)-3-Hydroxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-5-oxo-cyclopentyl]-hept-4-enoic acid methyl ester (78908-15-3,78908-16-4,78908-23-3,78908-26-6,78908-27-7,78963-82-3,81026-63-3,118456-55-6,130272-22-9,144371-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 1 h / Ambient temperature

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/jm00360a002

Reference yield:

(+/-)-methyl 7-(4-hydroxy-2-methoxy-5-oxo-1-cyclopenten-1-yl)-4(Z)-heptenoate (78908-09-5) → Enisoprost (81026-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / sodium dihydrobis(2-methoxyethoxy)aluminate / toluene / 3.25 h / -70 - 0 °C

2: imidazole / dimethylformamide / 1 h / Ambient temperature

3: 1.) n-BuLi, 2.) copper 1-pentyne, HMPT

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; copper 1-pentyne; sodium bis(2-methoxyethoxy)aluminium dihydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00360a002

upstream raw materials:

4-methyl-4-trimethylsilyloxyl-1-octyne

(+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-4(Z)-heptenoate

(1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene

(E)-1-(tri-n-butylstannyl)-4-methyl-4-<(trimethylsilyl)-oxy>-1-octene

Refernces

• 1、 Collins,Dajani,Pappo,Gasiecki,Bianchi,Woods. "Synthesis and gastric antisecretory properties of 4,5-unsaturated derivatives of 15-deoxy-16-hydroxy-16-methylprostaglandin E1". . p. 786 - 790. Retrieved 2007/10/02.