1-(2-Chloropropanoyl)indoline

Base Information

• Chemical Name: 1-(2-Chloropropanoyl)indoline
• CAS No.: 107236-27-1
• Molecular Formula: C11H12 Cl N O
• Molecular Weight: 209.67208
• Hs Code.: 2933990090
• European Community (EC) Number: 871-257-1
• DSSTox Substance ID: DTXSID70397590
• Mol file: 107236-27-1.mol

Synonyms:1-(2-chloropropanoyl)indoline;107236-27-1;2-Chloro-1-(indolin-1-yl)propan-1-one;2-chloro-1-(2,3-dihydroindol-1-yl)propan-1-one;2-chloro-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one;1H-Indole, 1-(2-chloro-1-oxopropyl)-2,3-dihydro- (9CI);SCHEMBL10836124;DTXSID70397590;MFCD05263162;AKOS000263281;AKOS017258633;SB65605;LS-06199;EN300-08435;SR-01000050451;SR-01000050451-1;Z56968826

Chemical Property of 1-(2-Chloropropanoyl)indoline

Chemical Property:

• PSA: 20.31000
• LogP: 2.26800
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 209.0607417
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

2-Chloro-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1CCC2=CC=CC=C21)Cl

Technology Process of 1-(2-Chloropropanoyl)indoline

There total 2 articles about 1-(2-Chloropropanoyl)indoline 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: 44.0%

1-indoline (496-15-1) + 2-chloropropionyl chloride (7623-09-8) → 2-chloro-1-(indolin-1-yl)propan-1-one (107236-27-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 0.75h;

DOI:10.1021/ja105148g

Reference yield: 44.0%

2-(triphenylphosphoranylideneamino)phenethyl 2-chloropropanoate (1297604-93-3) → 2-chloro-1-(indolin-1-yl)propan-1-one (107236-27-1)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 138 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0030-1259280

Reference yield: 70.0%

9-phenyl-9-borabicyclo[3.3.1]nonane (23418-91-9) + 2-chloro-1-(indolin-1-yl)propan-1-one (107236-27-1) → (S)-1-(indolin-1-yl)-2-phenylpropan-1-one (1239488-10-8)

Guidance literature:

With 2-methyl-propan-1-ol; nickel(II) chloride2-methoxyethyl ether; potassium tert-butylate; (1S,2S)-(+)-N,N'-dimethyl-1,2-bis[3-(trifluoromethyl)phenyl]-1,2-ethanediamine; In toluene; at -20 - -5 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja105148g

upstream raw materials:

1-indoline

2-chloropropionyl chloride

2-(triphenylphosphoranylideneamino)phenethyl 2-chloropropanoate

Downstream raw materials:

(S)-1-(indolin-1-yl)-2-phenylpropan-1-one

(R)-1-(indolin-1-yl)-2-phenylpropan-1-one

2-chloro-1-(indolin-1-yl)propan-1-one

2-chloro-1-(indolin-1-yl)propan-1-one

Refernces

• 1、 Lundin, Pamela M.,Fu, Gregory C.. "Asymmetric suzuki cross-couplings of activated secondary alkyl electrophiles: Arylations of racemic α-chloroamides". supporting information; experimental part. p. 11027 - 11029. Retrieved 2010/09/17.