2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile

Base Information

• Chemical Name: 2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile
• CAS No.: 58610-64-3
• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.239
• DSSTox Substance ID: DTXSID90360923
• Nikkaji Number: J2.666.148J
• Wikidata: Q82142951
• Mol file: 58610-64-3.mol

Synonyms:58610-64-3;2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile;7'-methyl-5'-oxo-3',5'-dihydro-2'H-spiro[[1,3]dioxolane-2,1'-indolizine]-6'-carbonitrile;7'-methyl-5'-oxospiro[1,3-dioxolane-2,1'-2,3-dihydroindolizine]-6'-carbonitrile;7-Methyl-5-oxo-2,3-dihydro-5H-spiro[indolizine-1,2'-[1,3]dioxolane]-6-carbonitrile;RQBNYJSVGQGNAA-UHFFFAOYSA-N;AGN-PC-0K1Y3B;SCHEMBL16649224;DTXSID90360923;MFCD00192042;SY316702;WS-01971;CS-0111318;FT-0667134;D85269;7 inverted exclamation mark -Methyl-5 inverted exclamation mark -oxo-3 inverted exclamation mark ,5 inverted exclamation mark -dihydro-2 inverted exclamation mark H-spiro[[1,3]dioxolane-2,1 inverted exclamation mark -indolizine]-6 inverted exclamation mark -carbonitrile;7'-Methyl-5'-oxo-2',3'-dihydrospiro[1,3-dioxolane-2,1'(5'H)- indolizine]-6'-carbonitrile;7'-Methyl-5'-oxo-3',5'-dihydro-2'H-spiro[[1,3]dioxolane-2,1'-indolizine]-6'-carbonitirile

Chemical Property of 2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile

Chemical Property:

• Solubility.: Dimethyl Sulfoxide
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 232.08479225
• Heavy Atom Count: 17
• Complexity: 503

Purity/Quality:

98% ^*data from raw suppliers

2'',3''-Dihydro-7''-methyl-5''-oxo-spiro[1,3-dioxolane-2,1''(5''H)-indolizine]-6''-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N2CCC3(C2=C1)OCCO3)C#N
• Uses: 7'-METHYL-5'-OXO-3',5'-DIHYDRO-2'H-SPIRO[[1,3]DIOXOLANE-2,1'-INDOLIZINE]-6'-CARBONITRILE is used in the preparation of Camptothecin derivatives, for their therapeutic use as antitumor agents.

Technology Process of 2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile

There total 4 articles about 2',3'-Dihydro-7'-methyl-5'-oxo-spiro[1,3-dioxolane-2,1'(5'H)-indolizine]-6'-carbonitrile 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: 93.0%

6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine (58610-63-2) + ethylene glycol (107-21-1) → 7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile (58610-64-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 20h; Heating;

DOI:10.1021/jm00179a016

Reference yield:

ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate (58610-61-0) → 7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile (58610-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K₂CO₃ / 1.) DMF, 45 deg C, 2.) DMF, 45 deg C, 40 h

2: 89 percent / conc. HCl / acetic acid / 2 h / Heating

3: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating

With hydrogenchloride; potassium carbonate; toluene-4-sulfonic acid; In acetic acid; toluene;

DOI:10.1021/jm00179a016

Reference yield:

2-(methoxycarbonyl)-6-cyano-7-methyl-1,5-dioxo-Δ6(8)-tetrahydroindolizine → 7’-methyl-5’-oxo-3’,5’-dihydro-2’H-spiro[[1,3]dioxolane-2,1‘-indolizine]-6’-carbonitrile (58610-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / conc. HCl / acetic acid / 2 h / Heating

2: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating

With hydrogenchloride; toluene-4-sulfonic acid; In acetic acid; toluene;

DOI:10.1021/jm00179a016

upstream raw materials:

6-cyano-7-methyl-1,5-dioxo-Δ⁶⁽⁸⁾-tetrahydroindolizine

ethylene glycol

ethyl 5-cyano-4-methyl-6-oxo-1, 6-dihydropyridine-2-carboxylate

methyl 6-cyano-1-hydroxy-7-methyl-5-oxo-3,5-dihydroindolizine-2-carboxylate

Downstream raw materials:

dl-10-hydroxycamptothecin

camptothecin

(2R)-1-(6′-cyano-5′-oxo-3′,5′,-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-2-ethoxy-2-oxoethyl 1-tosylpyrrolidine-2-carboxylate

(R)-((S)-2-(6′-cyano-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate