2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione

Base Information

• Chemical Name: 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione
• CAS No.: 3197-25-9
• Molecular Formula: C13H13NO3
• Molecular Weight: 231.251
• Hs Code.: 2925190090
• European Community (EC) Number: 608-687-4
• NSC Number: 38564
• DSSTox Substance ID: DTXSID60284708
• Nikkaji Number: J2.790.202B
• Wikidata: Q82019785
• ChEMBL ID: CHEMBL81412
• Mol file: 3197-25-9.mol

Synonyms:3197-25-9;2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione;2-(4-oxopentyl)isoindoline-1,3-dione;2-(4-oxopentyl)isoindole-1,3-dione;5-(N-PHTHALIMIDO)-2-PENTANONE;2-(4-Oxo-pentyl)-isoindole-1,3-dione;4-oxo-1-phthalimidopentane;2-(4-oxopentyl)-2,3-dihydro-1H-isoindole-1,3-dione;1- Phthalimido-4-pentanone;NSC38564;5-phthalimidyl-2-pentanone;1H-Isoindole-1,3(2H)-dione,2-(4-oxopentyl)-;CHEMBL81412;SCHEMBL2084857;DTXSID60284708;AMY40758;MFCD06797717;NSC 38564;NSC-38564;AKOS005072427;DD-0234;SB36564;2-(4-Oxopentyl)-2H-isoindole-1,3-dione;CS-0450946;FT-0619726;2-(4-oxidanylidenepentyl)isoindole-1,3-dione;EN300-96146;W10756;A823500;A875751;2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione #;J-506089;3-Furancarboxylic acid, 4-ethyl-2-methyl-, ethyl ester;F2189-0199;Z906137438

Chemical Property of 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione

Chemical Property:

• Vapor Pressure: 3.9E-06mmHg at 25°C
• Melting Point: 74-75 °C
• Refractive Index: 1.565
• Boiling Point: 385.104 °C at 760 mmHg
• Flash Point: 175.54 °C
• PSA: 54.45000
• Density: 1.238 g/cm³
• LogP: 1.58970
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 231.08954328
• Heavy Atom Count: 17
• Complexity: 327

Purity/Quality:

99%, ^*data from raw suppliers

2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCCN1C(=O)C2=CC=CC=C2C1=O
• Uses: 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione is an intermediate in synthesizing 5,6-Orthoquinone Primaquine-d6 Hydrobromide (O697512), an isotope labelled compound of 5,6-Orthoquinone Primaquine (O697510). 5,6-Orthoquinone Primaquine is used in the study of the differential pharmacological and toxicological properties of primaquine enantiomers. Primaquine is currently the only approved drug for the treatment and radical cure of Plasmodium vivax malaria.

Technology Process of 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione

There total 23 articles about 2-(4-Oxopentyl)-1H-isoindole-1,3(2H)-dione 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%

5-chloro-2-pentanone (5891-21-4) + phthalimide (136918-14-4,85-41-6) → 2-(4-oxopentyl)isoindole-1,3-dione (3197-25-9)

Guidance literature:

5-chloro-2-pentanone; phthalimide; With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20 - 80 ℃; for 18 - 24h;

With water; In DMF (N,N-dimethyl-formamide); at 0 - 5 ℃; for 1h;

Reference yield: 82.0%

2-(4-methoxypentyl)isoindoline-1,3-dione → 2-(4-oxopentyl)isoindole-1,3-dione (3197-25-9)

Guidance literature:

With calcium hypochlorite; acetic acid; In water; acetonitrile; at 0 ℃; regioselective reaction;

DOI:10.1021/acs.joc.7b00632

Reference yield: 81.0%

N-(pent-4-ynyl)phthalimide (6097-07-0) → 2-(4-oxopentyl)isoindole-1,3-dione (3197-25-9) + 2-(4-fluoropent-4-en-1-yl)isoindoline-1,3-dione

Guidance literature:

With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); hydrogen fluoride; water; In toluene; at 50 ℃; for 18h; chemoselective reaction; Sealed tube;

DOI:10.1002/chem.202103886

upstream raw materials:

5-chloro-2-pentanone

phthalimide

(4-phthalimido-butyryl)-malonic acid diethyl ester

potassium phtalimide

Downstream raw materials:

2-(2-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

4-methylhistamine

3-[imidazol-4⁽⁵⁾-yl]propylamine

Homohistamine dipicrate

Refernces

• 1、 Sundriyal, Sandeep,Moniot, Sébastien,Mahmud, Zimam,Yao, Shang,Di Fruscia, Paolo,Reynolds, Christopher R.,Dexter, David T.,Sternberg, Michael J. E.,Lam, Eric W.-F.,Steegborn, Clemens,Fuchter, Matthew J.. "Thienopyrimidinone Based Sirtuin-2 (SIRT2)-Selective Inhibitors Bind in the Ligand Induced Selectivity Pocket". . p. 1928 - 1945. Retrieved 2017.
• 2、 Bédard, Sandrine,Cavallo, Luigi,Falivene, Laura,Gauthier, Rapha?l,Nolan, Steven P.,Paquin, Jean-Fran?ois,Saab, Marina,Tzouras, Nikolaos V.,Van Hecke, Kristof,Zhang, Ziyun. "Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates". . . Retrieved 2021/12/09.
• 3、 -. "Substituted imidazo[4,5-c]quinoline macrocyclic compound as multi-target kinase inhibitor". Paragraph 0128-0131. . Retrieved 2020/04/17.