3-Benzyl-1,3-diazaspiro[4.5]decane-2,4-dione

Base Information

• Chemical Name: 3-Benzyl-1,3-diazaspiro[4.5]decane-2,4-dione
• CAS No.: 730-95-0
• Molecular Formula: C15H18N2O2
• Molecular Weight: 258.32
• DSSTox Substance ID: DTXSID90406572
• Nikkaji Number: J428.917J
• Wikidata: Q82211601
• Mol file: 730-95-0.mol

Synonyms:3-benzyl-1,3-diazaspiro[4.5]decane-2,4-dione;730-95-0;3-Benzyl-1,3-diazaspiro(4.5)decane-2,4-dione;NIOSH/HM2499410;DTXSID90406572;AKOS000835890;CS-0248900;HM24994100;EN300-41832;1,3-Diazaspiro(4.5)decane-2,4-dione, 3-benzyl-;Z16394888

Chemical Property of 3-Benzyl-1,3-diazaspiro[4.5]decane-2,4-dione

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 258.136827821
• Heavy Atom Count: 19
• Complexity: 368

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)C(=O)N(C(=O)N2)CC3=CC=CC=C3

Technology Process of 3-Benzyl-1,3-diazaspiro[4.5]decane-2,4-dione

There total 9 articles about 3-Benzyl-1,3-diazaspiro[4.5]decane-2,4-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: 81.0%

spiro(imidazolidine-4,1'-cyclohexane)-2,5-dione (702-62-5) + benzyl chloride (100-44-7) → 3-benzyl-1,3-diazaspiro[4.5]decane-2,4-dione (730-95-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 24h; Heating;

DOI:10.1002/jhet.5570210242

Reference yield: 78.0%

1-(3-benzyl-ureido)-cyclohexanecarboxylic acid ethyl ester (467443-11-4) → 3-benzyl-1,3-diazaspiro[4.5]decane-2,4-dione (730-95-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.3797/scipharm.aut-01-204

Reference yield:

phenylacetic acid (103-82-2) → 3-benzyl-1,3-diazaspiro[4.5]decane-2,4-dione (730-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride

2: sodium azide / toluene / 1 h / Heating

3: CHCl₃ / 3 h / 0 - 20 °C

4: 78 percent / aq. lithium hydroxide / tetrahydrofuran / 3 h / 0 - 20 °C

With lithium hydroxide; thionyl chloride; sodium azide; In tetrahydrofuran; chloroform; toluene;

DOI:10.3797/scipharm.aut-01-204

upstream raw materials:

spiro(imidazolidine-4,1'-cyclohexane)-2,5-dione

benzyl chloride

1-(3-benzyl-ureido)-cyclohexanecarboxylic acid ethyl ester

phenylacetic acid

Downstream raw materials:

3-Benzyl-1-butyl-1,3-diaza-spiro[4.5]decane-2,4-dione

3-Benzyl-4-hydroxy-1,3-diaza-spiro[4.5]decan-2-one

1,3-dibenzyl-1,3-diazaspiro[4.5]decane-2,4-dione

Refernces

• 1、 Nabil Aboul-Enein,El-Azzounya,Maklad,Attia,Wiese. "Synthesis, selective aldose reductase inhibitory profile and antihyperglycaemic potential of certain parabanic acid derivatives". . p. 329 - 350. Retrieved 2007/10/03.
• 2、 Pedregal,Trigo,Espada,et al.. "Some N3-substituted and N1,N3-disubstituted derivatives of cyclohexanespirohydantoin". . p. 477 - 480. Retrieved 2007/10/02.