1-Acetyl-6-iodoindoline

Base Information

• Chemical Name: 1-Acetyl-6-iodoindoline
• CAS No.: 115666-43-8
• Molecular Formula: C10H10INO
• Molecular Weight: 287.09700
• DSSTox Substance ID: DTXSID50470299
• Nikkaji Number: J2.387.116E
• Wikidata: Q82298359
• Mol file: 115666-43-8.mol

Synonyms:1-Acetyl-6-iodoindoline;115666-43-8;1-(6-iodo-2,3-dihydroindol-1-yl)ethanone;Ethanone, 1-(2,3-dihydro-6-iodo-1H-indol-1-yl)-;1H-Indole, 1-acetyl-2,3-dihydro-6-iodo-;SCHEMBL980588;DTXSID50470299;QYOUFIOXEFUHAU-UHFFFAOYSA-N;FT-0726984;1-(6-iodo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Chemical Property of 1-Acetyl-6-iodoindoline

Chemical Property:

• PSA: 20.31000
• LogP: 2.26520
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 286.98071
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

98%min ^*data from raw suppliers

1-Acetyl-6-iodoindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCC2=C1C=C(C=C2)I

Technology Process of 1-Acetyl-6-iodoindoline

There total 6 articles about 1-Acetyl-6-iodoindoline 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: 67.0%

1-acetyl-6-aminoindoline (62368-29-0) → 1-acetyl-2,3-dihydro-6-iodoindole (115666-43-8)

Guidance literature:

With toluene-4-sulfonic acid; potassium iodide; sodium nitrite; In water; acetonitrile; at 0 - 20 ℃; for 3.5h;

DOI:10.1002/ejoc.202101454

Reference yield: 43.0%

→ 1-acetyl-2,3-dihydro-6-iodoindole (115666-43-8)

Guidance literature:

Reference yield:

6-nitroindoline (19727-83-4) → 1-acetyl-2,3-dihydro-6-iodoindole (115666-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / pyridine / 1.4 h / 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 1.4 h / 20 °C

3: 62 percent / aq. NaNO₂; AcOH; KI / 24 h / 0 °C

With pyridine; hydrogen; acetic acid; potassium iodide; sodium nitrite; palladium on activated charcoal; In methanol;

DOI:10.1248/cpb.53.1277

upstream raw materials:

1-acetyl-6-aminoindoline

6-nitroindoline

1-acetyl-6-nitro-2,3-dihydroindole

6-nitroindole

Downstream raw materials:

6-iodo-2,3-dihydro-1H-indole

6-iodo-1 H-indole

(R,R)-3-{6-[3-(N-tert-butoxycarbonyl-2-methoxycarbonylmethylamino)-5-iodo-6-methoxyphenyl]indol-3-yl}-2-carbobenzyloxyaminopropionic acid tert-butyl ester

(R,R)-(6'-iodo-N-carbobenzyloxytryptophyl)-3',5'-dichloro-4'-hydroxyphenylglycine tert-butyl ester

Refernces

• 1、 -. "METHODS FOR TREATING HEPATITIS C". Page/Page column 447. . Retrieved 2010/10/20.
• 2、 Ohta, Toshiharu,Yamato, Yoshinori,Tahira, Hiroko,Somei, Masanori. "A REGIOSELECTIVE AND COMMON SYNTHETIC METHOD OF DIHALOGENOINDOLES AND ITS APPLICATION FOR THE TOTAL SYNTHESES OF MARINE ALKALOIDS, 4,6-DIBROMO-, 4,6-DIBROMO-2-METHYL-, 3,4,5-TRIBROMOINDOLE". . p. 2817 - 2822. Retrieved 2007/10/02.