11-Deoxy-PGE1

Base Information

• Chemical Name: 11-Deoxy-PGE1
• CAS No.: 37786-00-8
• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.488
• Hs Code.: 2918990090
• UNII: UG6237D2HO
• DSSTox Substance ID: DTXSID101317623
• Nikkaji Number: J355.526G
• Wikidata: Q27070753
• Pharos Ligand ID: LBZW7PD9DUYT
• Metabolomics Workbench ID: 2415
• ChEMBL ID: CHEMBL3246389
• Mol file: 37786-00-8.mol

Synonyms:11-deoxy-PGE1;11-deoxyprostaglandin E1;11-deoxyprostaglandin E1, (+-)-isomer;11-deoxyprostaglandin E1, (13E)-isomer;11-deoxyprostaglandin E1, (13E,15R)-(+-)-isomer;11-deoxyprostaglandin E1, (13E,15R)-isomer;11-deoxyprostaglandin E1, (13E,15S)-(+-)-isomer;doproston;doprostone

Chemical Property of 11-Deoxy-PGE1

Chemical Property:

• Vapor Pressure: 1.6E-12mmHg at 25°C
• Boiling Point: 509.7ºC
• Flash Point: 276.1 ºC
• PSA: 74.60000
• Density: 1.07 g/cm³
• LogP: 4.50430
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 338.24570956
• Heavy Atom Count: 24
• Complexity: 402

Purity/Quality:

99% ^*data from raw suppliers

11-deoxy Prostaglandin E1 ≥96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC(C=CC1CCC(=O)C1CCCCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1CCC(=O)[C@@H]1CCCCCCC(=O)O)O

Technology Process of 11-Deoxy-PGE1

There total 34 articles about 11-Deoxy-PGE1 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:

7-[(1S,2R)-2-((E)-(R)-3-Acetoxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester (23472-43-7,50484-52-1,84700-71-0,122221-47-0) → 7-[(1R,2S)-2-((E)-(S)-1-Hydroxy-oct-2-enyl)-5-oxo-cyclopentyl]-heptanoic acid (57755-79-0,57881-05-7,61476-09-3,61476-10-6,62182-70-1,62182-71-2,64091-38-9,78246-84-1,78246-85-2) + rac-11-deoxyprostaglandin-E1 (21269-27-2,30194-23-1,34603-80-0,37786-00-8,38380-61-9,39765-01-0,39765-13-4,39765-14-5,40098-34-8,41264-02-2,41692-82-4,41692-88-0,41692-89-1,52485-21-9,52485-24-2,52521-56-9,52521-58-1,53403-52-4,63229-83-4,95341-50-7,117182-90-8,135970-46-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 3h; Yield given. Yields of byproduct given;

Reference yield:

2-(6-Oxiranyl-hexyl)-cyclopent-2-enone (50999-74-1) → 7-[(S)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid (21269-27-2,30194-23-1,34603-80-0,37786-00-8,38380-61-9,39765-01-0,39765-13-4,39765-14-5,40098-34-8,41264-02-2,41692-82-4,41692-88-0,41692-89-1,52485-21-9,52485-24-2,52521-56-9,52521-58-1,53403-52-4,63229-83-4,95341-50-7,117182-90-8,135970-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) H₅IO₆, Et₂O, (ii) CrO₃, aq. H₂SO₄, acetone

2: diethyl ether

In diethyl ether;

DOI:10.1021/ja00837a028

Reference yield:

2-(6-Oxiranyl-hexyl)-cyclopent-2-enone (50999-74-1) → Doproston B (37786-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) H₅IO₆, Et₂O, (ii) CrO₃, aq. H₂SO₄, acetone

2: diethyl ether

In diethyl ether;

DOI:10.1021/ja00837a028

upstream raw materials:

2-(7-butoxycarbonylhexyl)-2-cyclopenten-1-one

(S)-3-(1-ethoxy-ethoxy)-1t-iodo-oct-1-ene

2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one

2-(6-Oxiranyl-hexyl)-cyclopent-2-enone

Downstream raw materials:

(S)-2-{7-[(1R,2R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoylamino}-3-phenyl-propionic acid

(S)-2-{7-[(1R,2R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoylamino}-3-phenyl-propionic acid methyl ester

(+/-)-15-epi-13.14-Dihydro-11-deoxy-PGE(1)

(+/-)-15-epi-11-deoxyprostaglandin F_1α

Refernces

• 1、 Freimanis, Ya. F.,Korits, V. R.,Sokolov, G. P.,Shatts, V. D.,Sakhartova, O. V.,et al.. "TOTAL SYNTHESIS AND PROPERTIES OF PROSTAGLANDINS. VII.* ISOMERIZATION OF(+/-)-11-DEOXYPROSTAGLANDIN-E1". . p. 1940 - 1946. Retrieved 2007/10/02.
• 2、 Dyadchenko, M. A.,Baslerova, Yu. A.,Grigor'ev, A. E.,Mel'nikova, V. I.,Pivnitskii, K. K.. "SYNTHESIS OF PROSTAGLANDINS VIA 8,13-CYCLOPROSTENOIC ACIDS. II. SYNTHESIS OF 11-DEOXYPROSTAGLANDINS E1 AND F1β BY THE EPOXIDATION AND REDUCTION OF 8,13-CYCLOPROST-14-ENOIC ACIDS". . p. 842 - 850. Retrieved 2007/10/02.