Spiro[cyclopropane-1,3'-indolin]-2'-one

Base Information

• Chemical Name: Spiro[cyclopropane-1,3'-indolin]-2'-one
• CAS No.: 13861-75-1
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 2933990090
• European Community (EC) Number: 866-659-9
• DSSTox Substance ID: DTXSID70507379
• Wikidata: Q82363572
• Mol file: 13861-75-1.mol

Synonyms:spiro(cyclopropane-1,3'-indolin)-2'-one

Chemical Property of Spiro[cyclopropane-1,3'-indolin]-2'-one

Chemical Property:

• Melting Point: 181-183 °C
• Boiling Point: 356.8±31.0 °C(Predicted)
• PKA: 14.07±0.20(Predicted)
• Flash Point: 207.8oC
• PSA: 29.10000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 1.80830
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 232

Purity/Quality:

95% ^*data from raw suppliers

Spiro[cyclopropane-1,3'-indolin]-2'-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC12C3=CC=CC=C3NC2=O

Technology Process of Spiro[cyclopropane-1,3'-indolin]-2'-one

There total 46 articles about Spiro[cyclopropane-1,3'-indolin]-2'-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: 97.6%

2-oxoindole (59-48-3) + ethylene dibromide (106-93-4) → spiro[cyclopropane-1,3'-indolin]-2'-one (13861-75-1)

Guidance literature:

2-oxoindole; With diisopropylamine; In tetrahydrofuran; at -20 - 20 ℃;

With n-butyllithium; In tetrahydrofuran; hexane; at -30 - 0 ℃; for 1h;

ethylene dibromide; In tetrahydrofuran; hexane; at 20 ℃; for 18h;

Reference yield: 92.0%

2H-indol-2-one (25250-89-9) + ethylene dibromide (106-93-4) → spiro[cyclopropane-1,3'-indolin]-2'-one (13861-75-1)

Guidance literature:

2H-indol-2-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -20 - 0 ℃; for 1h; Inert atmosphere;

ethylene dibromide; In tetrahydrofuran; at 0 - 20 ℃; for 22h;

Reference yield: 91.0%

2-oxoindole (59-48-3) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → spiro[cyclopropane-1,3'-indolin]-2'-one (13861-75-1)

Guidance literature:

With zinc trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 21 ℃; for 4h; Reagent/catalyst; Solvent;

DOI:10.1039/C6RA24985J

upstream raw materials:

1-cyano-1-phenylcyclopropane

1-(2-nitro-phenyl)-cyclopropanecarboxylic acid

1'-(2-bromoethyl)spiro-1,3'-<3H>-indole-2'(1'H)-one

3-(2-Chloro-ethyl)-1,3-dihydro-indol-2-one

Downstream raw materials:

N-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-2'-oxo-spiro[cyclopropane-1,3'-[3'H]indole]-1'(2'H)-carboxamide

6-nitro-1,2-dihydro-3-spiro-1'-cyclopropyl-1H-indole

5′-nitrospiro[cyclopropane-1,3′-indoline]-2′-one

C₁₀H₁₀N₂O

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