6-hydroxy-2,3-dihydro-1H-indolizin-5-one

Base Information

• Chemical Name: 6-hydroxy-2,3-dihydro-1H-indolizin-5-one
• CAS No.: 253195-68-5
• Molecular Formula: C8H9 N O2
• Molecular Weight: 151.16
• European Community (EC) Number: 816-849-2
• DSSTox Substance ID: DTXSID80444261
• Nikkaji Number: J1.977.460K
• Wikidata: Q82262352
• Mol file: 253195-68-5.mol

Synonyms:253195-68-5;6-hydroxy-2,3-dihydro-1H-indolizin-5-one;6-Hydroxy-2,3-dihydroindolizin-5(1H)-one;6-hydroxy-1,2,3,5-tetrahydroindolizin-5-one;DTXSID80444261;AKOS006281176;6-Hydroxy-1,2-dihydroindolizine-5(3H)-one;EN300-818849;Z1123694738

Chemical Property of 6-hydroxy-2,3-dihydro-1H-indolizin-5-one

Chemical Property:

• PSA: 42.23000
• LogP: 0.50010
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 265

Purity/Quality:

97% ^*data from raw suppliers

2,3-dihydro-6-hydroxy-5(1H)-Indolizinone 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=C(C(=O)N2C1)O

Technology Process of 6-hydroxy-2,3-dihydro-1H-indolizin-5-one

There total 4 articles about 6-hydroxy-2,3-dihydro-1H-indolizin-5-one 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: 91.0%

6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester (185198-42-9) → 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5)

Guidance literature:

With hydrogen bromide; In water; at 135 ℃; for 12h;

DOI:10.1021/jo9911600

Reference yield:

1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one (185198-40-7) → 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh(II)

2: hydrobromic acid / Heating

With hydrogen bromide; rhodium⁽²⁺⁾;

DOI:10.1021/jo0511492

Reference yield:

1-(phenylsulfonylacetyl)pyrrolidin-2-one (907969-47-5) → 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Et₃N; p-acetamidophenylsulfonyl azide / acetonitrile / 0 - 20 °C

2: 86 percent / Rh(OAc)2 / benzene / 14 h / Heating

3: 91 percent / HBr / H₂O / 12 h / 135 °C

With rhodium(II) acetate; 4-acetamidobenzenesulfonyl azide; hydrogen bromide; triethylamine; In water; acetonitrile; benzene; 1: Substitution / 2: Cycloaddition / 3: Decomposition;

DOI:10.1021/jo9911600

upstream raw materials:

6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid methyl ester

1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one

1-(phenylsulfonylacetyl)pyrrolidin-2-one

Downstream raw materials:

trifluoro-methanesulfonic acid 5-oxo-1,2,3,5-tetrahydro-indolizin-6-yl ester

ethyl 2-(4-methoxybenzyloxy)-4-(5-oxo-1,2,3,5-tetrahydroindolizin-6-yloxy)but-2-enoate

6-(2-trifluoromethyl-phenylamino)-2,3-dihydro-1H-indolizin-5-one

6-(3,5-dimethoxy-phenylamino)-2,3-dihydro-1H-indolizin-5-one

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